Halogen Alkoxy Spirocyclic Tetramic and Tetronic Acid Derivatives

ABSTRACT

The invention relates to novel haloalkoxyspirocyclic tetramic and tetronic acid derivatives of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which W, X, Y, Z, A, D, Q 1 , Q 2 , m and G have the meanings given above,
 
to a plurality of processes and intermediates for their preparation, and to their use as pesticides and/or herbicides.
 
     Moreover, the invention provides selective herbicidal compositions comprising, firstly, haloalkoxyspirocyclic tetramic and tetronic acid derivatives and, secondly, a crop plant compatibility-improving compound. 
     The invention furthermore relates to increasing the action of crop protection compositions comprising compounds of the formula (I) through the addition of ammonium salts or phosphonium salts and optionally penetrants.

The present invention relates to novel haloalkoxyspirocyclic tetramicand tetronic acid derivatives, to a plurality of processes for theirpreparation and to their use as pesticides and/or herbicides. Theinvention also provides selective herbicidal compositions comprising,firstly, haloalkoxyspirocyclic tetramic and tetronic acid derivativesand, secondly, a crop plant compatibility-improving compound.

The present invention furthermore relates to increasing the action ofcrop protection compositions comprising, in particular,haloalkoxyspirocyclic tetramic and tetronic acid derivatives, throughthe addition of ammonium salts or phosphonium salts and optionallypenetrants, to the corresponding compositions, to processes forproducing them and to their application in crop protection asinsecticides and/or acaricides and/or for preventing unwantedvegetation.

Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones have alreadybeen described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)).Furthermore, N-phenylpyrrolidine-2,4-diones have been synthesized by R.Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). Abiological activity of these compounds has not been described.

EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of a similarstructure (3-arylpyrrolidine-2,4-diones) of which, however, noherbicidal, insecticidal or acaricidal activity has become known.Unsubstituted bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355599, EP-A-415 211 and JP-A-12-053 670) and substituted monocyclic3-arylpyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077)are known to have herbicidal, insecticidal or acaridical activity.

Additionally known are polycyclic 3-arylpyrrolidine-2,4-dionederivatives (EP-A-442 073) and 1H-arylpyrrolidinedione derivatives(EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885,WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395,WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99/43649, WO99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO03/013249, WO 03/062244, WO 2004/007448, WO 2004/024 688, WO 04/065366,WO 04/080962, WO 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO05/049596, WO 05/066125, WO 05/092897, WO 06/000355, WO 06/029799, WO06/056281, WO 06/056282, WO 06/089633, WO 07/048,545, WO 07/073,856,DE-A-2005/059892, WO 07/096,058, WO 07/121,868, WO 07/140,881, WO08/067,873, WO 08/067,910 and WO 08/067,911. Furthermore known areketal-substituted 1H-arylpyrrolidine-2,4-diones from WO 99/16748 and(spiro)-ketal-substituted N-alkoxyalkoxy-substitutedarylpyrrolidinediones from JP-A-14 205 984 and Ito M. et. al.,Bioscience, Biotechnology and Biochemistry 67, 1230-1238, (2003). Theaddition of safeners to ketoenols is also known in principle from WO03/013249. Moreover, WO 06/024411 discloses herbicidal compositionscomprising ketoenols.

It is known that certain Δ³-dihydrofuran-2-one derivatives haveherbicidal, insecticidal or acaricidal properties: EP-A-528 156,EP-A-647 637, WO 95/26 954, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 98/06 721, WO99/16 748, WO 98/25 928, WO 99/43 649, WO 99/48 869, WO 99/55 673, WO01/23354, WO 01/74 770, WO 01/17 972, WO 04/024 688, WO 04/080 962, WO04/111 042, WO 05/092 897, WO 06/000 355, WO 06/029 799, WO 06/089633,WO 07/048,545 and WO 07/073,856 and WO 08/067,911.

However, the herbicidal and/or acaricidal and/or insecticidal activityand/or activity spectrum and/or the plant compatibility of the knowncompounds, in particular with respect to crop plants, is/are not alwayssatisfactory.

This invention, accordingly, provides novel compounds of the formula (I)

in which

-   W represents hydrogen, alkyl, alkenyl, alkynyl, optionally    substituted cycloalkyl, halogen, alkoxy, alkenyloxy, haloalkyl,    haloalkoxy or cyano,-   X represents halogen, alkyl, alkenyl, alkynyl, optionally    substituted cycloalkyl, alkoxy, alkenyloxy, alkylthio,    alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy,    nitro or cyano,-   Y and Z independently of one another represent hydrogen, alkyl,    alkenyl, alkynyl, optionally substituted cycloalkyl, alkoxy,    halogen, haloalkyl, haloalkoxy, cyano, nitro or in each case    optionally substituted aryl or hetaryl,-   A represents haloalkoxy or halocycloalkylalkoxy,-   D represents NH or oxygen,-   Q¹, Q² independently of one another represent hydrogen, alkyl,    haloalkyl or alkoxy,-   m represents the number 0 or 1,-   G represents hydrogen (a) or one of the groups

in which

-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulfur,-   M represents oxygen or sulfur,-   R¹ represents in each case optionally halogen- or cyano-substituted    alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or    represents in each case optionally halogen-, alkyl- or    alkoxy-substituted cycloalkyl or heterocyclyl or represents in each    case optionally substituted phenyl, phenylalkyl, hetaryl,    phenoxyalkyl or hetaryloxyalkyl,-   R² represents in each case optionally halogen- or cyano-substituted    alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each    case optionally substituted cycloalkyl, phenyl or benzyl,-   R³, R⁴ and R⁵ independently of one another represent in each case    optionally halogen-substituted alkyl, alkoxy, alkylamino,    dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent    in each case optionally substituted phenyl, benzyl, phenoxy or    phenylthio,-   R⁶ and R⁷ independently of one another represent hydrogen, in each    case optionally halogen- or cyano-substituted alkyl, cycloalkyl,    alkenyl, alkoxy, alkoxyalkyl, in each case optionally substituted    phenyl or benzyl, or together with the N atom to which they are    attached form an optionally substituted cycle which optionally    contains oxygen or sulfur.

Depending, inter alia, on the nature of the substituents, the compoundsof the formula (I) can be present as optical isomers or mixtures ofisomers in varying compositions, which can be separated, if desired, ina customary manner. The present invention provides both the pure isomersand the isomer mixtures, their preparation and use and compositionscomprising them. However, the following text will, for the sake ofsimplicity, always mention compounds of the formula (I), even thoughthis is understood as meaning not only the pure compounds, but also, ifappropriate, mixtures with various amounts of isomeric compounds.

Taking D to be NH (1) and D to be O (2), the following main structures(I-1) to (I-2) result:

in whichA, G, Q¹, Q², m, W, X, Y and Z have the meaning given above.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-1-a) to (I-1-g)result if D is NH (1),

in whichA, E, L, M, Q¹, Q², m, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe meanings given above.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-2-a) to (I-2-g)result if D is O (2),

in whichA, E, L, M, Q¹, Q², m, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe meaning given above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by the process described below:

-   (A) Compounds of the formula (I-1-a)

-   -   in which    -   A, Q¹, Q², m, W, X, Y and Z have the meanings given above,    -   are obtained when    -   compounds of the formula (II)

-   -   in which    -   A, Q¹, Q², m, W, X, Y and Z have the meanings given above,    -   and    -   R⁸ represents alkyl (preferably C₁-C₆-alkyl)    -   are subjected to an intramolecular condensation reaction in the        presence of a diluent and in the presence of a base.

-   (B) Furthermore, it has been found that compounds of the formula    (I-2-a)

-   -   in which    -   A, Q¹, Q², m, W, X, Y and Z have the meanings given above,    -   are obtained when    -   compounds of the formula (III)

-   -   in which    -   A, Q¹, Q², m, W, X, Y, Z and R⁸ have the meanings given above,    -   are subjected to an intramolecular condensation reaction in the        presence of a diluent and in the presence of a base.    -   Moreover, it has been found

-   (C) that the compounds of the formulae (I-1-b) to (I-2-b) shown    above in which R¹, A, Q¹, Q², m, W, X, Y and Z have the meanings    given above are obtained when compounds of the formulae (I-1-a) to    (I-2-a) shown above in which A, Q¹, Q², m, W, X, Y and Z have the    meanings given above are in each case    -   α) reacted with compounds of the formula (IV)

-   -   in which    -   R¹ is as defined above and    -   Hal represents halogen (in particular chlorine or bromine)    -   or    -   β) with carboxylic anhydrides of the formula (V)

R¹—CO—O—CO—R¹  (V)

-   -   in which    -   R¹ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (D) that the compounds of the formulae (I-1-c) to (I-2-c) shown    above in which R², A, Q¹, Q², m, W, M, X, Y and Z have the meanings    given above and L represents oxygen are obtained when compounds of    the formulae (I-1-a) to (I-2-a) shown above in which A, Q¹, Q², m,    W, X, Y and Z have the meanings given above are in each case    -   reacted with chloroformic esters or chloroformic thioesters of        the formula (VI)

R²—M—CO—Cl  (VI)

-   -   in which    -   R² and M have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (E) that compounds of the formulae (I-1-c) to (I-2-c) shown above in    which R², A, Q¹, Q², m, W, M, X, Y and Z have the meanings given    above and L represents sulfur are obtained when compounds of the    formulae (I-1-a) to (I-2-a) shown above in which A, Q¹, Q², m, W, X,    Y and Z have the meanings given above are in each case    -   reacted with chloromonothioformic esters or chlorodithioformic        esters of the formula (VII)

-   -   in which    -   M and R² have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (F) that compounds of the formulae (I-1-d) to (I-2-d) shown above in    which R³, A, W, Q¹, Q², m, X, Y and Z have the meanings given above    are obtained when compounds of the formulae (I-1-a) shown above to    (I-2-a) shown above in which A, B, Q¹, Q², m, W, X, Y and Z have the    meanings given above are in each case    -   reacted with sulfonyl chlorides of the formula (VIII)

R³—SO₂—Cl  (VIII)

-   -   in which    -   R³ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formulae (I-1-e) to (I-2-e) shown above in    which L, R⁴, R⁵, A, Q¹, Q², m, W, X, Y and Z have the meanings given    above are obtained when compounds of the formulae (I-1-a) to (I-2-a)    shown above in which A, Q¹, Q², m, W, X, Y and Z have the meanings    given above are in each case    -   reacted with phosphorus compounds of the formula (IX)

-   -   in which    -   L, R⁴ and R⁵ are as defined above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (H) that compounds of the formulae (I-1-f) to (I-2-f) shown above in    which E, A, Q¹, Q², m, W, X, Y and Z have the meanings given above    are obtained when compounds of the formulae (I-1-a) to (I-2-a) in    which A, Q¹, Q², m, W, X, Y and Z have the meanings given above are    in each case    -   reacted with metal compounds or amines of the formulae (X) or        (XI)

-   -   in which    -   Me represents a monovalent or divalent metal (preferably an        alkali metal or alkaline earth metal such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or        alkyl (preferably C₁-C₈-alkyl)    -   if appropriate in the presence of a diluent,

-   (I) that compounds of the formulae (I-1-g) to (I-2-g) shown above in    which L, R⁶, R⁷, A, Q¹, Q², m, W, X, Y and Z have the meanings given    above are obtained when compounds of the formulae (I-1-a) to (I-2-a)    shown above in which A, Q¹, Q², m, W, X, Y and Z have the meanings    given above are in each case    -   α) reacted with isocyanates or isothiocyanates of the formula        (XII)

R⁶—N═C=L  (XII)

-   -   in which    -   R⁶ and L are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or    -   β) reacted with carbamoyl chlorides or thiocarbamoyl chlorides        of the formula (XIII)

-   -   in which    -   L, R⁶ and R⁷ are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (Jα) that compounds of the formulae (I-1-a) to (I-1-g) shown above    in which A, D, G, Q¹, Q², m, W, X, Y and Z have the meaning given    above are obtained when compounds of the formulae (I-1-a′) to    (I-2-g′) in which A, D, G, Q¹, Q², m, W, X and Y have the meaning    given above and Z′ preferably represents bromine or iodine

-   -   and

-   (Jβ) that compounds of the formulae (I-1-a) to (I-2-g) shown above    in which A, D, G, Q¹, Q², m, W, X, Y and Z have the meaning given    above are obtained when compounds of the formulae (I-1-a″) to    (I-2-g″) in which A, D, G, Q¹, Q², m, W, X and Z have the meaning    given above and Y′ preferably represents bromine or iodine

-   -   are coupled with (het)aryl derivatives capable of coupling, for        example phenylboronic acids of the formulae (XVα) and (XVβ)

-   -   or esters thereof, in the presence of a solvent, in the presence        of a catalyst (for example Pd salts or Pd complexes) and in the        presence of a base (for example sodium carbonate, potassium        phosphate). Some of the compounds of the formula (XV) are known,        some are commercially available or can be prepared by processes        known in principle.

Furthermore, it has been found that the novel compounds of the formula(I) are very effective as pesticides, preferably as insecticides and/oracaricides and/or herbicides, and additionally are frequently toleratedvery well by plants, in particular by crop plants.

Surprisingly, it has now also been found that certainhaloalkoxyspirocyclic tetramic and tetronic acid derivatives, when usedtogether with the crop plant compatibility-improving compounds(safeners/antidotes) described below, efficiently prevent damage to thecrop plants and can be used in a particularly advantageous manner asbroad-spectrum combination preparations for the selective control ofunwanted plants in crops of useful plants, such as, for example, incereals, but also in corn, soybeans and rice.

The invention also provides selective herbicidal compositions comprisingan effective amount of an active compound combination comprising, ascomponents,

-   (a′) at least one compound of the formula (I) in which A, D, G, Q¹,    Q², m, W, X, Y and Z have the meaning given above    and-   (b) at least one crop plant compatibility-improving compound from    the following group of compounds:    4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),    1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[12-a]pyrimidin-6(2H)-one    (dicyclonon, BAS-145138),    4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine    (benoxacor), 1-methylhexyl 5-chloroquinoline-8-oxyacetate    (cloquintocet-mexyl—cf. also related compounds in EP-A-86750,    EP-A-94349, EP-A-191736, EP-A-492366),    3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron),    α-(cyanomethoximino)phenylacetonitrile (cyometrinil),    2,4-dichlorophenoxyacetic acid (2,4-D),    4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),    1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron,    dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),    S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate    (dimepiperate),    2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide    (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),    4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate    (fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 and    EP-A-346620), phenylmethyl    2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),    4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime    (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine    (furilazole, MON-13900), ethyl    4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate    (isoxadifen-ethyl—cf. also related compounds in WO-A-95/07897),    1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate    (lactidichlor), (4-chloro-o-tolyloxy)acetic acid (MCPA),    2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl    1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate    (mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),    2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),    2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),    1,8-naphthalic anhydride,    α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),    2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide    (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),    3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),    4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid,    diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl    diphenylmethoxyacetate, methyl    1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl    1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl    1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl    1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,    ethyl 1-(2,4-dichiorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf.    also related compounds in EP-A-269806 and EP-A-333131), ethyl    5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl    5-phenyl-2-isoxazoline-3-carboxylate, ethyl    5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. also    related compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl    5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl    5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl    5-chloroquinoline-8-oxyacetate, methyl    5-chloroquinoxaline-8-oxyacetate, ethyl    5-chloroquinoline-8-oxyacetate, allyl    5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl    5-chloroquinoline-8-oxyacetate, diethyl    5-chloroquinoline-8-oxymalonate, diallyl    5-chloroquinoxaline-8-oxymalonate, diethyl    5-chloroquinoline-8-oxymalonate (cf. also related compounds in    EP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, cf.    EP-A-613618), 4-chlorophenoxyacetic acid,    3,3′-dimethyl-4-methoxybenzophenone,    1-bromo-4-chloromethylsulfonylbenzene,    1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known    as    N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),    1-[4-(N-2-methoxybenzoylsulfamoyl)-phenyl]-3,3-dimethylurea,    1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,    1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,    N-(2-methoxy-5-methylbenzoyl)-4-(cyclo-propylaminocarbonyl)benzenesulfonamide,    and/or one of the following compounds, defined by general formulae,    of the general formula (IIa)

or of the general formula (IIb)

or of the formula (IIc)

where

-   m represents a number 0, 1, 2, 3, 4 or 5,-   A¹ represents one of the divalent heterocyclic groupings shown    below,

-   n represents a number 0, 1, 2, 3, 4 or 5,-   A² represents optionally C₁-C₄-alkyl- and/or C₁-C₄-alkoxycarbonyl-    and/or C₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2    carbon atoms,-   R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,-   R¹⁵ represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,-   R¹⁶ represents optionally fluorine-, chlorine- and/or    bromine-substituted C₁-C₄-alkyl,-   R¹⁷ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl,-   R¹⁸ represents hydrogen, in each case optionally fluorine-,    chlorine- and/or bromine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl or    C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, dioxolanyl-C₁-C₄-alkyl,    furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl, piperidinyl, or    optionally fluorine-, chlorine- and/or bromine- or    C₁-C₄-alkyl-substituted phenyl, R¹⁷ and R¹⁸ also together represent    C₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionally    substituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or    by two substituents which, together with the C atom to which they    are attached, form a 5- or 6-membered carbocycle,-   R¹⁹ represents hydrogen, cyano, halogen, or in each case optionally    fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl,    C₃-C₆-cycloalkyl or phenyl,-   R²⁰ represents hydrogen, in each case optionally hydroxyl-, cyano-,    halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl    or tri-(C₁-C₄-alkyl)silyl,-   R²¹ represents hydrogen, cyano, halogen, or in each case optionally    fluorine-, chlorine- and/or bromine-substituted C₁-C₄-alkyl,    C₃-C₆-cycloalkyl or phenyl,-   X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X² represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,-   X³ represents hydrogen, cyano, nitro, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,    and/or the following compounds, defined by general formulae,    of the general formula (IId)

or of the general formula (IIe)

where

-   t represents a number 0, 1, 2, 3, 4 or 5,-   v represents a number 0, 1, 2, 3, 4 or 5,-   R²² represents hydrogen or C₁-C₄-alkyl,-   R²³ represents hydrogen or C₁-C₄-alkyl,-   R²⁴ represents hydrogen, in each case optionally cyano-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, or in each case optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio or C₃-C₆-cycloalkylamino,-   R²⁵ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, or optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,-   R²⁶ represents hydrogen, optionally cyano-, hydroxyl-, halogen- or    C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each case optionally cyano-    or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl, optionally    cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl, or    optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-haloalkyl-,    C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally C₁-C₄-alkyl-substituted    C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl,-   X⁴ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy, and-   X⁵ represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl,    hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄ haloalkyl, C₁-C₄-alkoxy    or C₁-C₄-haloalkoxy.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicals givenin the formulae shown above and below are illustrated below:

-   W preferably represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, represents C₃-C₆-cycloalkyl which is optionally mono-    or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy, fluorine, chlorine,    trifluoromethyl or C₃-C₆-cycloalkyl, represents halogen,    C₁-C₆-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano,-   X preferably represents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, represents C₃-C₆-cycloalkyl which is optionally mono-    or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy, fluorine, chlorine,    trifluoromethyl or C₃-C₆-cycloalkyl, represents C₁-C₆-haloalkyl,    C₁-C₆-alkoxy, C₃-C₆-alkenyloxy, C₁-C₆-alkylthio,    C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkoxy,    C₃-C₆-haloalkenyloxy, nitro or cyano,-   Y and Z independently of one another preferably represent hydrogen,    halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, represent    C₃-C₆-cycloalkyl which is optionally mono- or disubstituted by    C₁-C₂-alkyl, C₁-C₂-alkoxy, fluorine, chlorine, trifluoromethyl or    C₃-C₆-cycloalkyl, represent C₁-C₆-alkoxy, C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, cyano, C₂-C₆-alkenyl, C₂-C₆-alkynyl or represent    one of the (het)aryl radicals

where in the case of (het)aryl only one of the radicals Y or Z mayrepresent (het)aryl,

-   V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,    C₁-C₆-alkylsulfonyl, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro,    cyano, or represents phenyl, phenoxy, phenoxy-C₁-C₄-alkyl,    phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl or    phenyl-C₁-C₄-alkylthio, each of which is optionally monosubstituted    or polysubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro or cyano,-   V² and V³ independently of one another represent hydrogen, halogen,    C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy,-   A preferably represents C₁-C₄-alkoxy which is mono- to    heptasubstituted by fluorine, chlorine, bromine and/or iodine or    represents C₃-C₆-cycloalkyl-C₁-C₂-alkoxy which is mono- to    pentasubstituted by fluorine, chlorine and/or bromine and which may    optionally be substituted by C₁-C₂-alkyl, C₁-C₂-haloalkyl or    C₁-C₂-alkoxy,-   D preferably represents NH (1) or oxygen (2),-   Q¹ and Q² independently of one another preferably represent    hydrogen, C₁-C₆-alkyl, C₁-C₂-haloalkyl or C₁-C₄-alkoxy,-   m preferably represents the number 0 or 1,-   G preferably represents hydrogen (a) or represents one of the groups

-   -   in which

-   E represents a metal ion or an ammonium ion,

-   L represents oxygen or sulfur and

-   M represents oxygen or sulfur,

-   R¹ preferably represents in each case optionally halogen- or    cyano-substituted C₁-C₂₀ alkyl, C₂-C₂₀-alkenyl,    C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl or    poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or represents optionally halogen-,    C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which    optionally one or two not directly adjacent methylene groups are    replaced by oxygen and/or sulfur,    -   represents phenyl which is optionally substituted by halogen,        cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,        C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl,    -   represents phenyl-C₁-C₆-alkyl which is optionally substituted by        halogen, nitro, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy,    -   represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or        6-membered hetaryl having one or two heteroatoms from the group        consisting of oxygen, sulfur and nitrogen,    -   represents phenoxy-C₁-C₆-alkyl which is optionally substituted        by halogen or C₁-C₆-alkyl,    -   represents optionally halogen-, amino- or        C₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl        having one or two heteroatoms from the group consisting of        oxygen, sulfur and nitrogen.

-   R² represents in each case optionally halogen- or cyano-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl or    poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,    -   represents C₃-C₈-cycloalkyl which is optionally substituted by        halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy,    -   represents phenyl or benzyl, each of which is optionally        substituted by halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkyl or C₁-C₆-halogenalkoxy,

-   R³ represents optionally halogen-substituted C₁-C₈-alkyl or in each    case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,    C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- or nitro-substituted    phenyl or benzyl.

-   R⁴ and R⁵ independently of one another preferably represent in each    case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio or    C₃-C₈-alkenylthio or represent in each case optionally halogen-,    nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-, C₁-C₄-alkylthio-,    C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- or C₁-C₄-haloalkyl-substituted    phenyl, phenoxy or phenylthio,

-   R⁶ and R⁷ independently of one another represent hydrogen, represent    in each case optionally halogen- or cyano-substituted C₁-C₈-alkyl,    C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl or    C₁-C₈-alkoxy-C₂-C₈-alkyl, represent in each case optionally    halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- or C₁-C₈-alkoxy-substituted    phenyl or benzyl or together represent an optionally    C₁-C₆-alkyl-substituted C₃-C₆-alkylene radical in which optionally    one methylene group is replaced by oxygen or sulfur.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   W particularly preferably represents hydrogen, chlorine, bromine,    C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-alkynyl, represents    C₃-C₆-cycloalkyl which is optionally monosubstituted by methyl,    ethyl, methoxy, fluorine, chlorine, trifluoromethyl or cyclopropyl,    represents C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,-   X particularly preferably represents chlorine, bromine, C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, represents C₃-C₆-cycloalkyl which is    optionally monosubstituted by methyl, ethyl, methoxy, fluorine,    chlorine, trifluoromethyl or cyclopropyl, represents C₁-C₄-alkoxy,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano,-   Y and Z independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, represent C₃-C₆-cycloalkyl which is    optionally monosubstituted by methyl, ethyl, methoxy, fluorine,    chlorine, trifluoromethyl or cyclopropyl, represents C₁-C₆-alkoxy,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano, C₂-C₄-alkenyl,    C₂-C₄-alkynyl or one of the (het)aryl radicals,

-   -   where in the case of (het)aryl only one of the radicals Y or Z        may represent (het)aryl,

-   V¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy, nitro, cyano or represents phenyl which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy, nitro    or cyano,

-   V² and V³ independently of one another particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,

-   A particularly preferably represents C₁-C₄-alkoxy which is mono- to    pentasubstituted by fluorine, chlorine and/or bromine or represents    C₃-C₆-cycloalkyl-C₁-C₂-alkoxy which is mono- to trisubstituted by    fluorine and/or chlorine,

-   D particularly preferably represents NH (1) or oxygen (2),

-   Q¹ and Q² independently of one another particularly preferably    represent hydrogen, methyl, ethyl, trifluoromethyl, methoxy or    ethoxy,

-   m particularly preferably represents the number 0 or 1,

-   G particularly preferably represents hydrogen (a) or represents one    of the groups

in which

-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulfur and-   M represents oxygen or sulfur,-   R¹ particularly preferably represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,    C₁-C₆-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkylthio-C₁-C₄-alkyl or    poly-C₁-C₆-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine or chlorine, or represents    C₃-C₇-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, C₁-C₅-alkyl or C₁-C₅-alkoxy and in which    optionally one or two not directly adjacent methylene groups are    replaced by oxygen and/or sulfur,    -   represents phenyl which is optionally mono- to trisubstituted by        fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy, C₁-C₄-alkylthio        or C₁-C₄-alkylsulfonyl,    -   represents phenyl-C₁-C₄-alkyl which is optionally mono- or        disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkoxy,        C₁-C₃-haloalkyl or C₁-C₃-haloalkoxy,    -   represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or        thienyl, each of which is optionally mono- or disubstituted by        fluorine, chlorine, bromine or C₁-C₄-alkyl,    -   represents phenoxy-C₁-C₅-alkyl which is optionally mono- or        disubstituted by fluorine, chlorine, bromine or C₁-C₄-alkyl or    -   represents pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkyl or        thiazolyloxy-C₁-C₅-alkyl, each of which is optionally mono- or        disubstituted by fluorine, chlorine, bromine, amino or        C₁-C₄-alkyl,-   R² particularly preferably represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,    C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl, each of    which is optionally mono- to trisubstituted by fluorine or chlorine,    -   represents C₃-C₇-cycloalkyl which is optionally mono- or        disubstituted by fluorine, chlorine, C₁-C₄-alkyl or C₁-C₄-alkoxy        or    -   represents phenyl or benzyl, each of which is optionally mono-        to trisubstituted by fluorine, chlorine, bromine, cyano, nitro,        C₁-C₄-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl or C₁-C₃-haloalkoxy,-   R³ particularly preferably represents C₁-C₆-alkyl which is    optionally mono- to trisubstituted by fluorine or chlorine, or    represents phenyl or benzyl, each of which is optionally mono- or    disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-haloalkyl, cyano or nitro,-   R⁴ and R⁵ independently of one another particularly preferably    represent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,    di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio, each of    which is optionally mono- to trisubstituted by fluorine or chlorine,    or represent phenyl, phenoxy or phenylthio, each of which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    nitro, cyano, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio,    C₁-C₃-haloalkylthio, C₁-C₃-alkyl or C₁-C₃-haloalkyl,-   R⁶ and R⁷ independently of one another particularly preferably    represent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy, C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, each of    which is optionally mono- to trisubstituted by fluorine or chlorine,    represent phenyl or benzyl, each of which is optionally mono- to    trisubstituted by fluorine, chlorine, bromine, C₁-C₅-haloalkyl,    C₁-C₅-alkyl or C₁-C₅-alkoxy, or together represent an optionally    C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally    one methylene group is replaced by oxygen or sulfur.

In the radical definitions mentioned as being particularly preferred,halogen represents fluorine, chlorine and bromine, in particularfluorine and chlorine.

-   W very particularly preferably represents hydrogen, chlorine,    bromine, methyl, ethyl, vinyl, ethynyl, propynyl, cyclopropyl,    methoxy, ethoxy or trifluoromethyl,-   X very particularly preferably represents chlorine, bromine, methyl,    ethyl, propyl, isopropyl, vinyl, ethynyl, propynyl, cyclopropyl,    methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy    or cyano,-   Y and Z independently of one another very particularly preferably    represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    vinyl, ethynyl, propynyl, cyclopropyl, methoxy, trifluoromethyl,    trifluoromethoxy, cyano or a phenyl radical,

-   -   where in the case of phenyl only one of the radicals Y or Z may        represent phenyl,

-   V¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, tert-butyl,    methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl or    trifluoromethoxy,

-   V² very particularly preferably represents hydrogen, fluorine,    chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or    trifluoromethyl,

-   A very particularly preferably represents methoxy, ethoxy, propoxy,    butoxy or isobutoxy, each of which is mono- to trisubstituted by    fluorine and/or chlorine, or represents cyclopropylmethoxy or    cyclopropylethoxy, each of which is mono- to trisubstituted by    fluorine and/or chlorine,

-   D very particularly preferably represents NH (1) or oxygen (2),

-   Q¹ and Q² very particularly preferably represent hydrogen,

-   m very particularly preferably represents the number 1

-   G very particularly preferably represents hydrogen (a) or represents    one of the groups

in which

-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulfur and-   M represents oxygen or sulfur,-   R¹ very particularly preferably represents C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,    C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally mono- to    trisubstituted by fluorine or chlorine, or represents    C₃-C₆-cycloalkyl which is optionally monosubstituted by fluorine,    chlorine, methyl, ethyl or methoxy,    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl,        n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or        trifluoromethoxy,    -   represents furanyl, thienyl or pyridyl, each of which is        optionally monosubstituted by chlorine, bromine or methyl,-   R² very particularly preferably represents C₁-C₁₀-alkyl,    C₂-C₁₀-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is    optionally mono- to trisubstituted by fluorine or chlorine,    -   represents cyclopentyl or cyclohexyl    -   or represents phenyl or benzyl, each of which is optionally        mono- or disubstituted by fluorine, chlorine, cyano, nitro,        methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,-   R³ very particularly preferably represents methyl, ethyl, propyl or    isopropyl, each of which is optionally mono- to trisubstituted by    fluorine or chlorine, or represents phenyl which is optionally    monosubstituted by fluorine, chlorine, bromine, methyl, ethyl,    isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl,    trifluoromethoxy, cyano or nitro,-   R⁴ and R⁵ independently of one another very particularly preferably    represent C₁-C₄-alkoxy or C₁-C₄-alkylthio, or represent phenyl,    phenoxy or phenylthio, each of which is optionally monosubstituted    by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy,    trifluoromethyl or trifluoromethoxy,-   R⁶ and R⁷ independently of one another very particularly preferably    represent hydrogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, represent phenyl which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    methyl, methoxy or trifluoromethyl, or together represent a    C₅-C₆-alkylene radical in which optionally one methylene group is    replaced by oxygen or sulfur.-   W especially preferably represents hydrogen, chlorine, bromine,    methyl, ethyl or methoxy, (particulary hydrogen, methyl or ethyl),-   X especially preferably represents chlorine, bromine, methyl, ethyl,    methoxy or ethoxy,-   Y and Z independently of one another especially preferably represent    hydrogen, chlorine, bromine, methyl, methoxy, cyclopropyl or the    radicals

-   -   where in this case only one of the radicals Y or Z may represent        a substituted phenyl radical, (Z particularly represents        hydrogen, methyl, 4-Cl-phenyl or 4-F-phenyl)

-   A especially preferably represents methoxy, ethoxy or propoxy, each    of which is mono- to trisubstituted by fluorine and/or chlorine (in    particular OCH₂CF₃ or OCH₂CF₂CF₃),

-   D especially preferably represents NH (1) or oxygen (2),

-   Q¹ and Q² especially preferably represent hydrogen,

-   m especially preferably represents the number 1,

-   G especially preferably represents hydrogen (a) or one of the groups

-   -   (in particular group a, b or c),

-   R¹ especially preferably represents C₁-C₁₀-alkyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, C₃-C₆-cycloalkyl,    -   represents phenyl which is optionally monosubstituted by        chlorine, or represents thienyl, (in particular C₁-C₁₀-alkyl),

-   R² especially preferably represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, or    benzyl, (in particular C₁-C₁₀-alkyl),

-   R³ especially preferably represents methyl,

-   R⁶ and R⁷ together especially preferably represent a C₅-C₆-alkylene    radical in which optionally one methylene group is replaced by    oxygen or sulfur.

The abovementioned general or preferred radical definitions orillustrations can be combined with one another as desired, i.e.including combinations between the respective ranges and preferredranges. They apply both to the end products and, correspondingly, toprecursors and intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Special preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being especially preferred.

Emphasis is given to compounds of the formula (I) in which G representshydrogen.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkanediylor alkenyl, can in each case be straight-chain or branched as far asthis is possible, including in combination with heteroatoms, such as,for example, in alkoxy.

Unless indicated otherwise, optionally substituted radicals may be mono-or polysubstituted, where in the case of polysubstitutions thesubstituents may be identical or different.

Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be specificallymentioned:

TABLE 1 (I-1-a)

A X W Y Z —O—CH₂—CF₃ CH₃ H H H —O—CH₂—CF₃ Br H H H —O—CH₂—CF₃ Cl H H H—O—CH₂—CF₃ CF₃ H H H —O—CH₂—CF₃ OCH₃ H H H —O—CH₂—CF₃ Br H Cl H—O—CH₂—CF₃ Cl H Br H —O—CH₂—CF₃ Cl H Cl H —O—CH₂—CF₃ Cl H CH₃ H—O—CH₂—CF₃ CH₃ H Cl H —O—CH₂—CF₃ Cl Cl H H —O—CH₂—CF₃ Cl OCH₃ H H—O—CH₂—CF₃ Cl CH₃ H H —O—CH₂—CF₃ Cl OC₂H₅ H H —O—CH₂—CF₃ OCH₃ OCH₃ H H—O—CH₂—CF₃ CH₃ CH₃ H H —O—CH₂—CF₃ C₂H₅ CH₃ H H —O—CH₂—CF₃ C₂H5 C₂H₅ H H—O—CH₂—CF₃ Br CH₃ Br H —O—CH₂—CF₃ Cl CH₃ Cl H —O—CH₂—CF₃ CH₃ Br CH₃ H—O—CH₂—CF₃ CH₃ Cl CH₃ H —O—CH₂—CF₃ OCH₃ CH₃ CH₃ H —O—CH₂—CF₃ OC₂H₅ CH₃CH₃ H —O—CH₂—CF₃ OC₃H₇ CH₃ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ CH₃ H —O—CH₂—CF₃ BrBr CH₃ H —O—CH₂—CF₃ Cl Cl CH₃ H —O—CH₂—CF₃ CH₃ CH₃ Br H —O—CH₂—CF₃ OCH₃C₂H₅ CH₃ H —O—CH₂—CF₃ OC₂H₅ C₂H₅ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ OCH₃ H—O—CH₂—CF₃ Br Cl CH₃ H —O—CH₂—CF₃ Br CH₃ Cl H —O—CH₂—CF₃ Cl CH₃ Br H—O—CH₂—CF₃ CH₃ CH₃ Cl H —O—CH₂—CF₃ C₂H₅ CH₃ CH₃ H —O—CH₂—CF₃ C₂H₅ C₂H₅CH₃ H —O—CH₂—CF₃ C₂H₅ CH₃ C₂H₅ H —O—CH₂—CF₃ C₂H₅ C₂H₅ C₂H₅ H —O—CH₂—CF₃C₂H₅ CH₃ Cl H —O—CH₂—CF₃ C₂H₅ C₂H₅ Cl H —O—CH₂—CF₃ C₂H₅ CH₃ Br H—O—CH₂—CF₃ C₂H₅ C₂H₅ Br H —O—CH₂—CF₃ C₂H₅ Cl CH₃ H —O—CH₂—CF₃ C₂H₅ BrCH₃ H —O—CH₂—CF₃ C₂H₅ Cl Cl H —O—CH₂—CF₃ C₂H₅ Br Br H —O—CH₂—CF₃ C₂H₅ ClBr H —O—CH₂—CF₃ C₂H₅ Br Cl H —O—CH₂—CF₃ OCH₃ CH₃ Cl H —O—CH₂—CF₃ OCH₃C₂H₅ Cl H —O—CH₂—CF₃ OC₂H₅ CH₃ Cl H —O—CH₂—CF₃ OC₂H₅ C₂H₅ Cl H—O—CH₂—CF₃ Cl OCH₃ CH₃ H —O—CH₂—CF₃ Cl OC₂H₅ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ ClH —O—CH₂—CF₃ Cl H Cl Cl —O—CH₂—CF₃ CH₃ H CH₃ CH₃ —O—CH₂—CF₃ CH₃ H Cl CH₃—O—CH₂—CF₃ Br H Cl CH₃ —O—CH₂—CF₃ Br H CH₃ CH₃ —O—CH₂—CF₃ Cl H Br CH₃—O—CH₂—CF₃ Cl H Cl CH₃ —O—CH₂—CF₃ CH₃ H Br CH₃ —O—CH₂—CF₃ Cl H CH₃ Cl—O—CH₂—CF₃ CH₃ H H CH₃ —O—CH₂—CF₃ Cl H H CH₃ —O—CH₂—CF₃ Br H H CH₃—O—CH₂—CF₃ CH₃ H H Cl —O—CH₂—CF₃ CH₃ H H Br —O—CH₂—CF₃ CH₃ CH₃ CH₃ CH₃—O—CH₂—CF₃ CH₃ CH₃ CH₃ F —O—CH₂—CF₃ CH₃ CH₃ CH₃ Cl —O—CH₂—CF₃ CH₃ CH₃CH₃ Br —O—CH₂—CF₃ CH₃ CH₃ H Cl —O—CH₂—CF₃ CH₃ CH₃ H Br —O—CH₂—CF₃ Cl ClH Br —O—CH₂—CF₃ CH₃ CH₃ 4-Cl—C₆H₄ H —O—CH₂—CF₃ C₂H₅ CH₃ 4-Cl—C₆H₄ H—O—CH₂—CF₃ C₂H₅ C₂H₅ 4-Cl—C₆H₄ H —O—CH₂—CF₃ Cl CH₃ 4-Cl—C₆H₄ H—O—CH₂—CF₃ Cl C₂H₅ 4-Cl—C₆H₄ H —O—CH₂—CF₃ CH₃ H H 4-Cl—C₆H₄ —O—CH₂—CF₃CH₃ CH₃ H 4-Cl—C₆H₄ —O—CH₂—CF₃ CH₃ H CH₃ 4-Cl—C₆H₄ —O—CH₂—CF₃ CH₃ CH₃CH₃ 4-Cl—C₆H₄ —O—CH₂—CF₃ Cl H H 4-Cl—C₆H₄ —O—CH₂—CF₃ I H H H —O—CH₂—CF₃I H CH₃ H —O—CH₂—CF₃ I CH₃ H H —O—CH₂—CF₃ I C₂H₅ H H —O—CH₂—CF₃ CH₃ H HI —O—CH₂—CF₃ CH₃ H CH₃ I —O—CH₂—CF₃ I CH₃ CH₃ H —O—CH₂—CF₃ I C₂H₅ CH₃ H—O—CH₂—CF₃ I CH₃ Cl H —O—CH₂—CF₃ I C₂H₅ Cl H —O—CH₂—CF₃ I Cl CH₃ H—O—CH₂—CF₃ I H CH₃ CH₃ —O—CH₂—CF₃ CH₃ H I H —O—CH₂—CF₃ C₂H₅ H I H—O—CH₂—CF₃ CH₃ CH₃ I H —O—CH₂—CF₃ C₂H₅ CH₃ I H —O—CH₂—CF₃ C₂H₅ C₂H₅ I H—O—CH₂—CF₃ Cl CH₃ I H —O—CH₂—CF₃ Cl C₂H₅ I H —O—CH₂—CF₃ CH₃ H I CH₃—O—CH₂—CF₃ CH₃ CH₃ H I —O—CH₂—CF₃ I H H CH₃ —O—CH₂—CF₃ C₂H₅ H H H—O—CH₂—CF₃

H H H —O—CH₂—CF₃

CH₃ H H —O—CH₂—CF₃

H CH₃ H —O—CH₂—CF₃

C₂H₅ H H —O—CH₂—CF₃

CH₃ CH₃ H —O—CH₂—CF₃

C₂H₅ CH₃ H —O—CH₂—CF₃

CH₃ Cl H —O—CH₂—CF₃

C₂H₅ Cl H —O—CH₂—CF₃

Cl CH₃ H —O—CH₂—CF₃ CH₃ H

H —O—CH₂—CF₃ C₂H₅ H

H —O—CH₂—CF₃ CH₃ CH₃

H —O—CH₂—CF₃ C₂H₅ CH₃

H —O—CH₂—CF₃ C₂H₅ C₂H₅

H —O—CH₂—CF₃ Cl CH₃

H —O—CH₂—CF₃ Cl C₂H₅

H

Besides the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2-a) may be specificallymentioned:

TABLE 2 (I-2-a)

A X W Y Z —O—CH₂—CF₃ CH₃ H H H —O—CH₂—CF₃ Br H H H —O—CH₂—CF₃ Cl H H H—O—CH₂—CF₃ CF₃ H H H —O—CH₂—CF₃ OCH₃ H H H —O—CH₂—CF₃ Br H Cl H—O—CH₂—CF₃ Cl H Br H —O—CH₂—CF₃ Cl H Cl H —O—CH₂—CF₃ Cl H CH₃ H—O—CH₂—CF₃ CH₃ H Cl H —O—CH₂—CF₃ Cl Cl H H —O—CH₂—CF₃ Cl OCH₃ H H—O—CH₂—CF₃ Cl CH₃ H H —O—CH₂—CF₃ Cl OC₂H₅ H H —O—CH₂—CF₃ OCH₃ OCH₃ H H—O—CH₂—CF₃ CH₃ CH₃ H H —O—CH₂—CF₃ C₂H₅ CH₃ H H —O—CH₂—CF₃ C₂H₅ C₂H₅ H H—O—CH₂—CF₃ Br CH₃ Br H —O—CH₂—CF₃ Cl CH₃ Cl H —O—CH₂—CF₃ CH₃ Br CH₃ H—O—CH₂—CF₃ CH₃ Cl CH₃ H —O—CH₂—CF₃ OCH₃ CH₃ CH₃ H —O—CH₂—CF₃ OC₂H₅ CH₃CH₃ H —O—CH₂—CF₃ OC₃H₇ CH₃ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ CH₃ H —O—CH₂—CF₃ BrBr CH₃ H —O—CH₂—CF₃ Cl Cl CH₃ H —O—CH₂—CF₃ CH₃ CH₃ Br H —O—CH₂—CF₃ OCH₃C₂H₅ CH₃ H —O—CH₂—CF₃ OC₂H₅ C₂H₅ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ OCH₃ H—O—CH₂—CF₃ Br Cl CH₃ H —O—CH₂—CF₃ Br CH₃ Cl H —O—CH₂—CF₃ Cl CH₃ Br H—O—CH₂—CF₃ CH₃ CH₃ Cl H —O—CH₂—CF₃ C₂H₅ CH₃ CH₃ H —O—CH₂—CF₃ C₂H₅ C₂H₅CH₃ H —O—CH₂—CF₃ C₂H₅ CH₃ C₂H₅ H —O—CH₂—CF₃ C₂H₅ C₂H₅ C₂H₅ H —O—CH₂—CF₃C₂H₅ CH₃ Cl H —O—CH₂—CF₃ C₂H₅ C₂H₅ Cl H —O—CH₂—CF₃ C₂H₅ CH₃ Br H—O—CH₂—CF₃ C₂H₅ C₂H₅ Br H —O—CH₂—CF₃ C₂H₅ Cl CH₃ H —O—CH₂—CF₃ C₂H₅ BrCH₃ H —O—CH₂—CF₃ C₂H₅ Cl Cl H —O—CH₂—CF₃ C₂H₅ Br Br H —O—CH₂—CF₃ C₂H₅ ClBr H —O—CH₂—CF₃ C₂H₅ Br Cl H —O—CH₂—CF₃ OCH₃ CH₃ Cl H —O—CH₂—CF₃ OCH₃C₂H₅ Cl H —O—CH₂—CF₃ OC₂H₅ CH₃ Cl H —O—CH₂—CF₃ OC₂H₅ C₂H₅ Cl H—O—CH₂—CF₃ Cl OCH₃ CH₃ H —O—CH₂—CF₃ Cl OC₂H₅ CH₃ H —O—CH₂—CF₃ CH₃ CH₃ ClH —O—CH₂—CF₃ Cl H Cl Cl —O—CH₂—CF₃ CH₃ H CH₃ CH₃ —O—CH₂—CF₃ CH₃ H Cl CH₃—O—CH₂—CF₃ Br H Cl CH₃ —O—CH₂—CF₃ Br H CH₃ CH₃ —O—CH₂—CF₃ Cl H Br CH₃—O—CH₂—CF₃ Cl H Cl CH₃ —O—CH₂—CF₃ CH₃ H Br CH₃ —O—CH₂—CF₃ Cl H CH₃ Cl—O—CH₂—CF₃ CH₃ H H CH₃ —O—CH₂—CF₃ Cl H H CH₃ —O—CH₂—CF₃ Br H H CH₃—O—CH₂—CF₃ CH₃ H H Cl —O—CH₂—CF₃ CH₃ H H Br —O—CH₂—CF₃ CH₃ CH₃ CH₃ CH₃—O—CH₂—CF₃ CH₃ CH₃ CH₃ F —O—CH₂—CF₃ CH₃ CH₃ CH₃ Cl —O—CH₂—CF₃ CH₃ CH₃CH₃ Br —O—CH₂—CF₃ CH₃ CH₃ H Cl —O—CH₂—CF₃ CH₃ CH₃ H Br —O—CH₂—CF₃ Cl ClH Br —O—CH₂—CF₃ CH₃ CH₃ 4-Cl—C₆H₄ H —O—CH₂—CF₃ C₂H₅ CH₃ 4-Cl—C₆H₄ H—O—CH₂—CF₃ C₂H₅ C₂H₅ 4-Cl—C₆H₄ H —O—CH₂—CF₃ Cl CH₃ 4-Cl—C₆H₄ H—O—CH₂—CF₃ Cl C₂H₅ 4-Cl—C₆H₄ H —O—CH₂—CF₃ CH₃ H H 4-Cl—C₆H₄ —O—CH₂—CF₃CH₃ CH₃ H 4-Cl—C₆H₄ —O—CH₂—CF₃ CH₃ H CH₃ 4-Cl—C₆H₄ —O—CH₂—CF₃ CH₃ CH₃CH₃ 4-Cl—C₆H₄ —O—CH₂—CF₃ Cl H H 4-Cl—C₆H₄ —O—CH₂—CF₃ I H H H —O—CH₂—CF₃I H CH₃ H —O—CH₂—CF₃ I CH₃ H H —O—CH₂—CF₃ I C₂H₅ H H —O—CH₂—CF₃ CH₃ H HI —O—CH₂—CF₃ CH₃ H CH₃ I —O—CH₂—CF₃ I CH₃ CH₃ H —O—CH₂—CF₃ I C₂H₅ CH₃ H—O—CH₂—CF₃ I CH₃ Cl H —O—CH₂—CF₃ I C₂H₅ Cl H —O—CH₂—CF₃ I Cl CH₃ H—O—CH₂—CF₃ I H CH₃ CH₃ —O—CH₂—CF₃ CH₃ H I H —O—CH₂—CF₃ C₂H₅ H I H—O—CH₂—CF₃ CH₃ CH₃ I H —O—CH₂—CF₃ C₂H₅ CH₃ I H —O—CH₂—CF₃ C₂H₅ C₂H₅ I H—O—CH₂—CF₃ Cl CH₃ I H —O—CH₂—CF₃ Cl C₂H₅ I H —O—CH₂—CF₃ CH₃ H I CH₃—O—CH₂—CF₃ CH₃ CH₃ H I —O—CH₂—CF₃ I H H CH₃ —O—CH₂—CF₃

H H H —O—CH₂—CF₃

CH₃ H H —O—CH₂—CF₃

H CH₃ H —O—CH₂—CF₃

C₂H₅ H H —O—CH₂—CF₃

CH₃ CH₃ H —O—CH₂—CF₃

C₂H₅ CH₃ H —O—CH₂—CF₃

CH₃ Cl H —O—CH₂—CF₃

C₂H₅ Cl H —O—CH₂—CF₃

Cl CH₃ H —O—CH₂—CF₃ CH₃ H

H —O—CH₂—CF₃ C₂H₅ H

H —O—CH₂—CF₃ CH₃ CH₃

H —O—CH₂—CF₃ C₂H₅ CH₃

H —O—CH₂—CF₃ C₂H₅ C₂H₅

H —O—CH₂—CF₃ Cl CH₃

H —O—CH₂—CF₃ Cl C₂H₅

H

Preferred definitions of the groups listed above in connection with thecrop plant compatibility-improving compounds (“herbicide safeners”) ofthe formulae (II), (IIb), (IIc), (IId) and (IIe) are defined below.

-   m preferably represents the number 0, 1, 2, 3 or 4.-   A¹ preferably represents one of the divalent heterocyclic groupings    shown below,

-   n preferably represents the number 0, 1, 2, 3 or 4.-   A² preferably represents in each case optionally methyl-, ethyl-,    methoxycarbonyl-, ethoxycarbonyl- or allyloxycarbonyl-substituted    methylene or ethylene.-   R¹⁴ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, s- or t-butoxy, methylthio, ethylthio,    n- or i-propylthio, n-, s- or t-butylthio, methylamino, ethylamino,    n- or i-propylamino, n-, s- or t-butylamino, dimethylamino or    diethylamino.-   R¹⁵ preferably represents hydroxyl, mercapto, amino, methoxy,    ethoxy, n- or i-propoxy, n-, s- or t-butoxy, 1-methylhexyloxy,    allyloxy, 1-allyloxymethylethoxy, methylthio, ethylthio, n- or    i-propylthio, n-, s- or t-butylthio, methylamino, ethylamino, n- or    i-propylamino, n-, s- or t-butylamino, dimethylamino or    diethylamino.-   R¹⁶ preferably represents in each case optionally fluorine-,    chlorine-, and/or bromine-substituted methyl, ethyl, n- or i-propyl.-   R¹⁷ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, s- or t-butyl-substituted phenyl.-   R¹⁸ preferably represents hydrogen, in each case optionally    fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    n-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl,    methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,    dioxolanylmethyl, furyl, furyl-methyl, thienyl, thiazolyl,    piperidinyl, or optionally fluorine-, chlorine-, methyl-, ethyl-, n-    or i-propyl-, n-, s- or t-butyl-substituted phenyl, or together with    R¹⁷ represents one of the radicals —CH₂—O—CH₂—CH₂— and    —CH₂—CH₂—O—CH₂—CH₂— which are optionally substituted by methyl,    ethyl, furyl, phenyl, a fused benzene ring or by two substituents    which, together with the C atom to which they are attached, form a    5- or 6-membered carbocycle.-   R¹⁹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl,    cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   R²⁰ preferably represents hydrogen, in each case optionally    hydroxyl-, cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, s- or    t-butyl.-   R²¹ preferably represents hydrogen, cyano, fluorine, chlorine,    bromine, or represents in each case optionally fluorine-, chlorine-    and/or bromine-substituted methyl, ethyl, n- or i-propyl, n-, s- or    t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.-   X¹ preferably represents nitro, cyano, fluorine, chlorine, bromine,    methyl, ethyl, n- or i-propyl, n-, s- or t-butyl, difluoromethyl,    dichloromethyl, trifluoromethyl, trichloromethyl,    chloro-difluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X² preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoromethoxy or trifluoromethoxy.-   X³ preferably represents hydrogen, nitro, cyano, fluorine, chlorine,    bromine, methyl, ethyl, n- or i-propyl, n-, s- or t-butyl,    difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,    chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or    i-propoxy, difluoro-methoxy or trifluoromethoxy.-   t preferably represents the number 0, 1, 2, 3 or 4.-   v preferably represents the number 0, 1, 2 or 3.-   R²² preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²³ preferably represents hydrogen, methyl, ethyl, n- or i-propyl.-   R²⁴ preferably represents hydrogen, in each case optionally cyano-,    fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted    methyl, ethyl, n- or i-propyl, n-, s- or t-butyl, methoxy, ethoxy,    n- or i-propoxy, n-, s- or t-butoxy, methylthio, ethylthio, n- or    i-propylthio, n-, s- or t-butylthio, methylamino, ethylamino, n- or    i-propylamino, n-, s- or t-butylamino, dimethylamino or    diethylamino, or in each case optionally cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted    cyclopropyl, cyclobutyl, cyclo-pentyl, cyclohexyl, cyclopropyloxy,    cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclo-propylthio,    cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino,    cyclobutyl-amino, cyclopentylamino or cyclohexylamino.-   R²⁵ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, or in    each case optionally cyano-, fluorine-, chlorine-, bromine-,    methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl.-   R²⁶ preferably represents hydrogen, in each case optionally cyano-,    hydroxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or    i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or    s-butyl, in each case optionally cyano-, fluorine-, chlorine- or    bromine-substituted propenyl, butenyl, propynyl or butynyl, in each    case optionally cyano-, fluorine-, chlorine-, bromine-, methyl-,    ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl, or optionally nitro-, cyano-, fluorine-,    chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, s- or    t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,    difluoromethoxy- or trifluoromethoxy-substituted phenyl, or together    with R²⁵ represents in each case optionally methyl- or    ethyl-substituted butane-1,4-diyl (trimethylene), pentane-1,5-diyl,    1-oxabutane-1,4-diyl or 3-oxapentane-1,5-diyl.-   X⁴ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, s- or t-butyl, trifluoromethyl, methoxy,    ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.-   X⁵ preferably represents nitro, cyano, carboxyl, carbamoyl, formyl,    sulfamoyl, hydroxyl, amino, fluorine, chlorine, bromine, methyl,    ethyl, n- or i-propyl, n-, s- or t-butyl, trifluoromethyl, methoxy,    ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.

Examples of the compounds of the formula (IIa) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIa) (IIa)

Ex- (Posi- ample tions) No. (X¹)_(m) A¹ R¹⁴ IIa-1 (2) Cl, (4) Cl

OCH₃ IIa-2 (2) Cl, (4) Cl

OCH₃ IIa-3 (2) Cl, (4) Cl

OC₂H₅ IIa-4 (2) Cl, (4) Cl

OC₂H₅ IIa-5 (2) Cl

OCH₃ IIa-6 (2) Cl, (4) Cl

OCH₃ IIa-7 (2) F

OCH₃ IIa-8 (2) F

OCH₃ IIa -9 (2) Cl, (4) Cl

OC₂H₅ IIa-10 (2) Cl, (4) CF₃

OCH₃ IIa-11 (2) Cl

OCH₃ IIa-12 —

OC₂H₅ IIa -13 (2) Cl, (4) Cl

OC₂H₅ IIa-14 (2) Cl, (4) Cl

OC₂H₅ IIa -15 (2) Cl, (4) Cl

OC₂H₅ IIa-16 (2) Cl, (4) Cl

OC₂H₅ IIa-17 (2) Cl, (4) Cl

OC₂H₅ IIa-18 —

OH

Examples of the compounds of the formula (IIb) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIb) (IIb)

Exam- (Posi- (Posi- ple tion) tion) No. X² X³ A² R¹⁵ IIb-1 (5) Cl — CH₂OH IIb-2 (5) Cl — CH₂ OCH₃ IIb-3 (5) Cl — CH₂ OC₂H₅ IIb-4 (5) Cl — CH₂OC₃H₇-n IIb-5 (5) Cl — CH₂ OC₃H₇-i IIb-6 (5) Cl — CH₂ OC₄H₉-n IIb-7 (5)Cl — CH₂ OCH(CH₃)C₅H₁₁-n IIb-8 (5) Cl (2) F CH₂ OH IIb-9 (5) Cl (2) ClCH₂ OH IIb- 10 (5) Cl — CH₂ OCH₂CH═CH₂ IIb- 11 (5) Cl — CH₂ OC₄H₉-i IIb-12 (5) Cl — CH₂

IIb- 13 (5) Cl —

OCH₂CH═CH₂ IIb- 14 (5) Cl —

OC₂H₅ IIb- 15 (5) Cl —

OCH₃

Examples of the compounds of the formula (IIc) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIc) (IIc)

Example No. R¹⁶ N(R¹⁷, R¹⁸) IIc-1 CHCl₂ N(CH₂CH═CH₂)₂ IIc-2 CHCl₂

IIc-3 CHCl₂

IIc-4 CHCl₂

IIc-5 CHCl₂

IIc-6 CHCl₂

IIc-7 CHCl₂

Examples of the compounds of the formula (IId) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IId) (IId)

Ex- (Posi- (Posi- ample tions) tions) No. R²² R²³ R²⁴ (X⁴)_(t) (X⁵)_(v)IId-1 H H CH₃ (2) OCH₃   IId-2 H H C₂H₅ (2) OCH₃ — IId-3 H H C₃H₇-n (2)OCH₃ — IId-4 H H C₃H₇-i (2) OCH₃ — IId-5 H H

(2) OCH₃ — IId-6 H H CH₃ (2) OCH₃ (5) CH₃ — IId-7 H H C₂H₅ (2) OCH₃ (5)CH₃ — IId-8 H H C₃H₇-n (2) OCH₃ (5) CH₃ — IId-9 H H C₃H₇-i (2) OCH₃ (5)CH₃ — IId-10 H H

(2) OCH₃ (5) CH₃ — IId-11 H H OCH₃ (2) OCH₃ (5) CH₃ — IId-12 H H OC₂H₅(2) OCH₃ (5) CH₃ — IId-13 H H OC₃H₇-i (2) OCH₃ (5) CH₃ — IId-14 H H SCH₃(2) OCH₃ (5) CH₃ — IId-15 H H SC₂H₅ (2) OCH₃ (5) CH₃ — IId-16 H HSC₃H₇-i (2) OCH₃ (5) CH₃ — IId-17 H H NHCH₃ (2) OCH₃ (5) CH₃ — IId-18 HH NHC₂H₅ (2) OCH₃ (5) CH₃ — IId-19 H H NHC₃H₇-i (2) OCH₃ (5) CH₃ —IId-20 H H

(2) OCH₃ (5) CH₃ — IId-21 H H NHCH₃ (2) OCH₃ — IId-22 H H NHC₃H₇-i (2)OCH₃ — IId-23 H H N(CH₃)₂ (2) OCH₃ — IId-24 H H N(CH₃)₂ (3) CH₃ (4) CH₃— IId-25 H H CH₂—O—CH₃ (2) OCH₃ —

Examples of the compounds of the formula (IIe) which are veryparticularly preferred as herbicide safeners according to the inventionare listed in the table below.

TABLE Examples of the compounds of the formula (IIe) (IIe)

Exam- (Posi- (Posi- ple tions) tions) No. R²² R²⁵ R²⁶ (X⁴)_(t) (X⁵)_(v)IIe-1 H H CH₃ (2) OCH₃ — IIe-2 H H C₂H₅ (2) OCH₃ — IIe-3 H H C₃H₇-n (2)OCH₃ — IIe-4 H H C₃H₇-i (2) OCH₃ — IIe-5 H H

(2) OCH₃ — IIe-6 H CH₃ CH₃ (2) OCH₃ — IIe-7 H H CH₃ (2) OCH₃ (5) CH₃ —IIe-8 H H C₂H₅ (2) OCH₃ (5) CH₃ — IIe-9 H H C₃H₇-n (2) OCH₃ (5) CH₃ —IIe-10 H H C₃H₇-i (2) OCH₃ (5) CH₃ — IIe-11 H H

(2) OCH₃ (5) CH₃ — IIe-12 H CH₃ CH₃ (2) OCH₃ (5) CH₃ —

Most preferred as crop plant compatibility-improving compound [component(b′)] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, dimepiperateand the compounds IIe-5 and IIe-11, and particular emphasis is given tocloquintocet-mexyl and mefenpyr-diethyl.

The compounds of the general formula (IIa) to be used according to theinvention as safeners are known and/or can be prepared by processesknown per se (cf. WO-A-91/07874, WO-A-95/07897).

The compounds of the general formula (IIb) to be used according to theinvention as safeners are known and/or can be prepared by processesknown per se (cf. EP-A-191736).

The compounds of the general formula (IIc) to be used according to theinvention as safeners are known and/or can be prepared by processesknown per se (cf. DE-A-2218097, DE-A-2350547).

The compounds of the general formula (IId) to be used according to theinvention as safeners are known and/or can be prepared by processesknown per se (cf. DE-A-19621522/U.S. Pat. No. 6,235,680).

The compounds of the general formula (IIe) to be used according to theinvention as safeners are known and can be prepared by processes knownper se (cf. WO-A-99/66795/U.S. Pat. No. 6,251,827).

Examples of the selective herbicidal combinations according to theinvention comprising in each case one active compound of the formula (I)and in each case one of the safeners defined above are listed in thetable below.

TABLE Examples of combinations according to the invention Activecompounds of the formula (I) Safeners I-1-a cloquintocet-mexyl I-1-afenchlorazole-ethyl I-1-a isoxadifen-ethyl I-1-a mefenpyr-diethyl I-1-afurilazole I-1-a fenclorim I-1-a cumyluron I-1-a daimuron/dymron I-1-adimepiperate I-1-a IIe-11 I-1-a IIe-5 I-1-b cloquintocet-mexyl I-1-bfenchlorazole-ethyl I-1-b isoxadifen-ethyl I-1-b mefenpyr-diethyl I-1-bfurilazole I-1-b fenclorim I-1-b cumyluron I-1-b daimuron/dymron I-1-bdimepiperate I-1-b IIe-11 I-1-b IIe-5 I-1-c cloquintocet-mexyl I-1-cfenchlorazole-ethyl I-1-c isoxadifen-ethyl I-1-c mefenpyr-diethyl I-1-cfurilazole I-1-c fenclorim I-1-c cumyluron I-1-c daimuron/dymron I-1-cdimepiperate I-1-c IIe-5 I-1-c IIe-11 I-1-d cloquintocet-mexyl I-1-dfenchlorazole-ethyl I-1-d isoxadifen-ethyl I-1-d mefenpyr-diethyl I-1-dfurilazole I-1-d fenclorim I-1-d cumyluron I-1-d daimuron/dymron I-1-ddimepiperate I-1-d IIe-11 I-1-d IIe-5 I-1-e cloquintocet-mexyl I-1-efenchlorazole-ethyl I-1-e isoxadifen-ethyl I-1-e mefenpyr-diethyl I-1-efurilazole I-1-e fenclorim I-1-e cumyluron I-1-e daimuron/dymron I-1-edimepiperate I-1-e IIe-5 I-1-e IIe-11 I-1-f cloquintocet-mexyl I-1-ffenchlorazole-ethyl I-1-f isoxadifen-ethyl I-1-f mefenpyr-diethyl I-1-ffurilazole I-1-f fenclorim I-1-f cumyluron I-1-f daimuron/dymron I-1-fdimepiperate I-1-f IIe-5 I-1-f IIe-11 I-1-g cloquintocet-mexyl I-1-gfenchlorazole-ethyl I-1-g isoxadifen-ethyl I-1-g mefenpyr-diethyl I-1-gfurilazole I-1-g fenclorim I-1-g cumyluron I-1-g daimuron/dymron I-1-gdimepiperate I-1-g IIe-5 I-1-g IIe-11 I-2-a cloquintocet-mexyl I-2-afenchlorazole-ethyl I-2-a isoxadifen-ethyl I-2-a mefenpyr-diethyl I-2-afurilazole I-2-a fenclorim I-2-a cumyluron I-2-a daimuron/dymron I-2-adimepiperate I-2-a IIe-5 I-2-a IIe-11 I-2-b cloquintocet-mexyl I-2-bfenchlorazole-ethyl I-2-b isoxadifen-ethyl I-2-b mefenpyr-diethyl I-2-bfurilazole I-2-b fenclorim I-2-b cumyluron I-2-b daimuron/dymron I-2-bdimepiperate I-2-b IIe-5 I-2-b IIe-11 I-2-c cloquintocet-mexyl I-2-cfenchlorazole-ethyl I-2-c isoxadifen-ethyl I-2-c mefenpyr-diethyl I-2-cfurilazole I-2-c fenclorim I-2-c cumyluron I-2-c daimuron/dymron I-2-cdimepiperate I-2-c IIe-5 I-2-c IIe-11 I-2-d cloquintocet-mexyl I-2-dfenchlorazole-ethyl I-2-d isoxadifen-ethyl I-2-d mefenpyr-diethyl I-2-dfurilazole I-2-d fenclorim I-2-d cumyluron I-2-d daimuron/dymron I-2-ddimepiperate I-2-d IIe-5 I-2-d IIe-11 I-2-e cloquintocet-mexyl I-2-efenchlorazole-ethyl I-2-e isoxadifen-ethyl I-2-e mefenpyr-diethyl I-2-efurilazole I-2-e fenclorim I-2-e cumyluron I-2-e daimuron/dymron I-2-edimepiperate I-2-e IIe-5 I-2-e IIe-11 I-2-f cloquintocet-mexyl I-2-ffenchlorazole-ethyl I-2-f isoxadifen-ethyl I-2-f mefenpyr-diethyl I-2-ffurilazole I-2-f fenclorim I-2-f cumyluron I-2-f daimuron/dymron I-2-fdimepiperate I-2-f IIe-5 I-2-f IIe-11 I-2-g cloquintocet-mexyl I-2-gfenchlorazole-ethyl I-2-g isoxadifen-ethyl I-2-g mefenpyr-diethyl I-2-gfurilazole I-2-g fenclorim I-2-g cumyluron I-2-g daimuron/dymron I-2-gdimepiperate I-2-g IIe-5 I-2-g IIe-11

Surprisingly, it has now been found that the active compoundcombinations defined above of compounds of the general formula (I) andsafeners (antidotes) from the group (b′) set out above combine very gooduseful plant tolerance with a particularly high herbicidal activity andcan be used in various crops, in particular in cereals (especiallywheat), but also in soya, potatoes, corn and rice, for the selectivecontrol of weeds.

In this context it is to be considered surprising that, from amultiplicity of known safeners or antidotes capable of antagonizing thedamaging effect of a herbicide on the crop plants, it is specificallythe compounds of group (b′) set out above which are suitable forcompensating—almost completely—the damaging effect ofhaloalkoxyspirocyclic tetramic and tetronic acid derivatives on the cropplants, without at the same time having any critical adverse effect onthe herbicidal activity against the weeds.

Emphasis may be given here to the particularly advantageous effect ofthe particularly preferred and most preferred combination partners fromgroup (b′), in particular with regard to the gentle treatment of cerealplants, such as wheat, barley and rye, for example, but also corn andrice, as crop plants.

In the literature it has already been described how the action ofvarious active compounds can be increased by addition of ammonium salts.The salts in question, however, are detersive salts (e.g. WO 95/017817)or salts which have relatively long alkyl substituents and/or arylsubstituents and which have a permeabilizing action or which increasethe solubility of the active compound (e.g. EP-A 0 453 086, EP-A 0 664081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No. 5,462,912,U.S. Pat. No. 5,538,937, US-A 03/0224939, US-A 05/0009880, US-A05/0096386). Furthermore, the prior art describes the activity only forcertain active compounds and/or certain applications of thecorresponding compositions. In yet further cases, these are salts ofsulfonic acids where the acids for their part have a paralyzing actionon insects (U.S. Pat. No. 2,842,476). An increase in action by ammoniumsulfate, for example, is described by way of example for the herbicidesglyphosate and phosphinothricin and for phenyl-substituted cyclicketoenols (U.S. Pat. No. 6,645,914, EP-A2 0 036 106, WO 07/068,427). Acorresponding increase in action in the case of insecticides isdescribed for certain cyclic ketoenols in WO 07/068,428.

The use of ammonium sulfate as a formulating assistant has also beendescribed for certain active compounds and applications (WO 92/16108),but its purpose therein is to stabilize the formulation, not to increasethe action.

It has now been found, likewise surprisingly, that the action ofinsecticides and/or acaricides and/or herbicides from the class of thehaloalkoxyspirocyclic tetramic and tetronic acid derivatives can beincreased significantly by the addition of ammonium salts or phosphoniumsalts to the application solution or by the incorporation of these saltsinto a formulation comprising haloalkoxyspirocyclic tetramic andtetronic acid derivatives of the formula (I). The present inventiontherefore provides for the use of ammonium salts or phosphonium saltsfor increasing the action of crop protection compositions which compriseas their active compound herbicidal and/or insecticidal and/oracaricidal haloalkoxyspirocyclic tetramic and tetronic acid derivativesof the formula (I). The invention likewise provides compositions whichcomprise herbicidal and/or acaricidal and/or insecticidalhaloalkoxyspirocyclic tetramic and tetronic acid derivatives of theformula (I) and action-increasing ammonium salts or phosphonium salts,including both formulated active compounds and also ready-to-usecompositions (spray liquors). The invention further provides, finally,for the use of these compositions for controlling insect pests and/orspider mites and/or unwanted vegetation.

The compounds of the formula (I) possess a broad insecticidal and/oracaricidal and/or herbicidal activity, but individually the activityand/or plant tolerance leaves something to be desired. However, byadding ammonium or phosphonium salts, some or all of these propertiescan be improved.

The active compounds can be used in the compositions of the invention ina broad concentration range. The concentration of the active compoundsin the formulation is typically 0.1%-50% by weight.

Ammonium salts and phosphonium salts which, according to the invention,increase the activity of crop protection compositions comprising activecompounds from the class of the haloalkoxyspirocyclic tetramic acid andtetronic acid derivatives of the formula (I) are defined by formula(III′)

in which

-   D represents nitrogen or phosphorus,-   D preferably represents nitrogen,-   R^(26′), R²⁷, R²⁸ and R²⁹ independently of one another represent    hydrogen or in each case optionally substituted C₁-C₈-alkyl or mono-    or polyunsaturated, optionally substituted C₁-C₈-alkylene, the    substituents being selectable from halogen, nitro and cyano,-   R^(26′), R²⁷, R²⁸ and R²⁹ independently of one another preferably    represent hydrogen or in each case optionally substituted    C₁-C₄-alkyl, the substituents being selectable from halogen, nitro    and cyano,-   R^(26′), R²⁷, R²⁸ and R²⁹ independently of one another particularly    preferably represent hydrogen, methyl, ethyl, n-propyl, isopropyl,    n-butyl, isobutyl, sec-butyl or tert-butyl,-   R^(26′), R²⁷, R²⁸ and R²⁹ very particularly preferably represent    hydrogen,-   n represents 1, 2, 3 or 4,-   n preferably represents 1 or 2,-   R³⁰ represents an inorganic or organic anion,-   R³⁰ preferably represents bicarbonate, tetraborate, fluoride,    bromide, iodide, chloride, monohydrogenphosphate,    dihydrogenphosphate, hydrogensulfate, tartrate, sulfate, nitrate,    thiosulfate, thiocyanate, formate, lactate, acetate, propionate,    butyrate, pentanoate or oxalate,-   R³⁰ particularly preferably represents lactate, sulfate, nitrate,    thiosulfate, thiocyanate, oxalate or formate,-   R³⁰ very particularly preferably represents sulfate.

Inventively emphasized combinations of active compound, salt andpenetrant are listed in the table below. “Penetrant as per test” meanshere that any compound that acts as a penetrant in the cuticlepenetration test (Baur et al., 1997, Pesticide Science 51, 131-152) issuitable.

The ammonium salts and phosphonium salts of the formula (III′) can beused in a broad concentration range to increase the activity of cropprotection compositions comprising ketoenols. In general, the ammoniumsalts or phosphonium salts are used in the ready-to-use crop protectioncomposition in a concentration of from 0.5 to 80 mmol/l, preferably 0.75to 37.5 mmol/l, particularly preferably 1.5 to 25 mmol/l. In the case ofa formulated product, the concentration of ammonium salt and/orphosphonium salt in the formulation is selected such that it is withinthese stated general, preferred or particularly preferred rangesfollowing dilution of the formulation to the desired active compoundconcentration. The concentration of the salt in the formulation here isusually 1-50% by weight.

In one preferred embodiment of the invention, it is not only an ammoniumsalt and/or a phosphonium salt, but additionally a penetrant, that isadded to the crop protection compositions to boost the activity. It isconsidered entirely surprising that even in these cases an even greaterincrease in activity is observed. The present invention thereforelikewise provides for the use of a combination of penetrant and ammoniumsalts and/or phosphonium salts to increase the activity of cropprotection compositions which comprise herbicidal and/or acaricidaland/or insecticidal, haloalkoxyspirocyclic tetramic and tetronic acidderivatives of the formula (I) as active compound. The inventionlikewise provides compositions which comprise herbicidal and/oracaricidal and/or insecticidal haloalkoxyspirocyclic tetramic andtetronic acid derivatives of the formula (I), penetrants and ammoniumsalts or phosphonium salts, including both formulated active compoundsand also ready-to-use compositions (spray liquors). Finally, theinvention also provides the use of these compositions for controllingharmful insects and/or spider mites.

Suitable penetrants in the present context are all those substanceswhich are usually used for improving the penetration of agrochemicalactive compounds into plants. Penetrants are defined in this context bytheir ability to penetrate from the aqueous spray liquor and/or from thespray coating into the cuticle of the plant and thereby increase themobility of active compounds in the cuticle. The method described in theliterature (Baur et al., 1997, Pesticide Science 51, 131-152) can beused for determining this property.

Suitable penetrants are, for example, alkanol alkoxylates. Penetrantsaccording to the invention are alkanol alkoxylates of the formula (IV′)

R—O-(-AO)_(v)—R′  (IV′)

in which

-   R represents straight-chain or branched alkyl having 4 to 20 carbon    atoms,-   R′ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, tert-butyl, n-pentyl or n-hexyl,-   AO represents an ethylene oxide radical, a propylene oxide radical,    a butylene oxide radical or mixtures of ethylene oxide and propylene    oxide radicals or butylene oxide radicals and-   v represents a number from 2 to 30.

A preferred group of penetrants are alkanol alkoxylates of the formula

R—O-(-EO-)_(n)-R′  (IV′-a)

in which

-   R has the meaning given above,-   R′ has the meaning given above,-   EO represents —CH₂—CH₂—O— and-   n represents a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-EO-)_(p)-(-PO-)_(q)-R′  (IV′-b)

in which

-   R has the meaning given above,-   R′ has the meaning given above,-   EO represents —CH₂—CH₂—O—,-   PO represents

-   p represents a number from 1 to 10 and-   q represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-PO-)_(r)-(EO-)_(s)-R′  (IV′-c)

in which

-   R has the meaning given above,-   R′ has the meaning given above,-   EO represents —CH₂—CH₂—O—,-   PO represents

-   r represents a number from 1 to 10 and-   s represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-EO-)_(p)-(-BO-)_(q)-R′  (IV′-d)

in which

-   R and R′ have the meanings given above,-   EO represents —CH₂—CH₂—O—,-   BO represents

-   p represents a number from 1 to 10 and-   q represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

R—O-(-BO-)_(r)-(-EO-)_(s)-R′  (IV′-e)

in which

-   R and R′ have the meanings given above,-   BO represents

-   EO represents —CH₂—CH₂—O—,-   r represents a number from 1 to 10 and-   s represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformula

CH₃—(CH₂)_(t)—CH₂—O-(-CH₂—CH₂—O-)_(u)-R′  (IV′-f)

in which

-   R′ has the meaning given above,-   t represents a number from 8 to 13,-   u represents a number from 6 to 17.

In the formulae given above,

-   R preferably represents butyl, isobutyl, n-pentyl, isopentyl,    neopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl,    nonyl, isononyl, decyl, n-dodecyl, isododecyl, lauryl, myristyl,    isotridecyl, trimethylnonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (IV-c), mentionmay be made of 2-ethyl-hexyl alkoxylate of the formula

in which

-   EO represents —CH₂—CH₂—O—,-   PO represent

andthe numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (IV-d), mentionmay be made of the formula

CH₃—(CH₂)₁₀—O-(-EO-)₆-(-BO-)₂—CH₃  (IV′-d-1)

in which

-   EO represents —CH₂—CH₂—O—,-   BO represents

andthe numbers 10, 6 and 2 represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) arecompounds of this formula in which

-   t represents a number from 9 to 12 and-   u represents a number from 7 to 9.

With very particular preference, mention may be made of alkanolalkoxylate of the formula (IV′-f-1)

CH₃—(CH₂)_(t)—CH₂—O-(-CH₂—CH₂—O-)_(u)-H  (IV′-f-1)

in which

-   t represents the average value 10.5 and-   u represents the average value 8.4.

The above formulae provide general definitions of the alkanolalkoxylates. These substances are mixtures of substances of the statedtype with different chain lengths. The indices are therefore averagevalues which may also deviate from whole numbers.

The alkanol alkoxylates of the stated formulae are known, and some ofthem are commercially available or can be prepared by known methods (cf.WO 98/35 553, WO 00/35 278 and EP-A 0 681 865)

Suitable penetrants also include, for example, substances which promotethe availability of the compounds of the formula (I) in the spraycoating. These include, for example, mineral and vegetable oils.Suitable oils are all mineral or vegetable oils—modified orotherwise—which can usually be used in agrochemical compositions. By wayof example, mention may be made of sunflower oil, rapeseed oil, oliveoil, castor oil, colza oil, corn seed oil, cottonseed oil and soybeanoil or the esters of said oils. Preference is given to rapeseed oil,sunflower oil and their methyl or ethyl esters.

The concentration of penetrant in the compositions of the invention canbe varied within a wide range. In the case of a formulated cropprotection composition, it is generally 1 to 95% by weight, preferably 1to 55% by weight, particularly preferably 15-40% by weight. In theready-to-use compositions (spray liquors), the concentration isgenerally between 0.1 and 10 g/l, preferably between 0.5 and 5 g/l.

Crop protection compositions of the invention may also comprise furthercomponents, examples being surfactants and/or dispersing assistants oremulsifiers.

Suitable nonionic surfactants and/or dispersing assistants include allsubstances of this type that can typically be used in agrochemicalcompositions. Mention may preferably be made of polyethyleneoxide-polypropylene oxide block copolymers, polyethylene glycol ethersof linear alcohols, reaction products of fatty acids with ethylene oxideand/or propylene oxide, and also polyvinyl alcohol,polyvinylpyrrolidone, copolymers of polyvinyl alcohol andpolyvinylpyrrolidone, and copolymers of (meth)acrylic acid and(meth)acrylic esters, and additionally alkyl ethoxylates and alkylarylethoxylates, which optionally may be phosphated and optionally may beneutralized with bases, mention being made, by way of example, ofsorbitol ethoxylates, and also polyoxyalkylenamine derivatives.

Suitable anionic surfactants include all substances of this type thatcan typically be used in agrochemical compositions. Preference is givento alkali metal salts and alkaline earth metal salts of alkylsulfonicacids or alkylarylsulfonic acids.

A further preferred group of anionic surfactants and/or dispersingassistants are the following salts that are of low solubility invegetable oil: salts of polystyrenesulfonic acids, salts ofpolyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehydecondensation products, salts of condensation products ofnaphthalenesulfonic acid, phenolsulfonic acid and formaldehyde, andsalts of lignosulfonic acid.

Suitable additives which may be included in the formulations of theinvention are emulsifiers, foam inhibitors, preservatives, antioxidants,colorants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products ofalkylphenols with ethylene oxide and/or propylene oxide, ethoxylatedarylalkylphenols, and also ethoxylated and propoxylatedarylalkylphenols, and also sulfated or phosphated arylalkyl ethoxylatesand/or arylalkyl ethoxypropoxylates, mention being made by way ofexample of sorbitan derivatives, such as polyethylene oxide-sorbitanfatty acid esters, and sorbitan fatty acid esters.

Using, in accordance with process (A), for example ethylN-[(4-chloro-2,6-dimethyl)-phenylacetyl]-1-amino-4-trifluoroethoxycyclohexanecarboxylateas starting material, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, in accordance with process (B), for example ethylO-[(2-chloro-6-methyl)phenylacetyl]-1-hydroxy-4-trifluoroethoxycyclohexanecarboxylate,the course of the process according to the invention can be representedby the following reaction scheme:

Using, in accordance with process (Cα), for example8-trifluoroethoxy-3-[(4-chloro-2,6-dimethyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, in accordance with process (C) (variant β), for example8-trifluoroethoxy-3-[(2,4-dichloro)phenyl]-1-oxaspiro[4,5]decane-2,4-dioneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, in accordance with process (D), for example8-trifluoroethoxy-3-[(2,4-dichloro-6-methyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand ethyl chloroformate as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, in accordance with process (E), for example8-trifluoroethoxy-3-[(2,4,6-trimethyl)phenyl]-1-oxaspiro[4,5]decane-2,4-dioneand methyl chloromonothioformate as starting materials, the course ofthe reaction can be represented as follows:

Using, in accordance with process (F), for example8-trifluoroethoxy-3-[(2,4,6-trimethyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand methanesulfonyl chloride as starting materials, the course of thereaction can be represented by the following reaction scheme:

Using, in accordance with process (G), for example8-trifluoroethoxy-3-[(2,4-dichloro-6-methyl)-phenyl]-1-oxaspiro[4,5]decane-2,4-dioneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by thefollowing reaction scheme:

Using, in accordance with process (H), for example8-trifluoroethoxy-3-[(2,3,4,6-tetramethylphenyl]-1-azaspiro[4,5]decane-2,4-dioneand NaOH as components, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, in accordance with process (I) (variant α), for example8-trifluoroethoxy-3-[(2,4,5-trimethyl)phenyl]-1-oxaspiro[4,5]decane-2,4-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the following reaction scheme:

Using, in accordance with process (I) (variant β), for example8-trifluoroethoxy-3-[(2,4,6-trimethyl)phenyl]-1-azaspiro[4,5]decane-2,4-dioneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

Using, in accordance with process (Jβ), for example8-trifluoroethoxy-3-[(4-bromo-2,6-dimethyl-phenyl)]-1-azaspiro[4,5]decane-2,4-dioneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

The compounds of the formula (II)

in whichA, Q¹, Q², m, W, X, Y, Z and R⁸ have the meanings given above,are novel.

The acylamino acid esters of the formula (II) are obtained, for example,when amino acid derivatives of the formula (XVI)

in whichA, m, Q¹ and Q² and R⁸ have the meaning given above,are acylated with substituted phenylacetic acid derivatives of theformula (XVII)

in which

-   W, X, Y and Z have the meanings given above and-   U represents a leaving group introduced by reagents for the    activation of carboxylic acids, such as carbonyldiimidazole,    carbonyldiimides (such as, for example, dicyclohexylcarbodiimide),    phosphorylating agents (such as, for example, POCl₃, BOP-Cl),    halogenating agents, such as, for example thionyl chloride, oxalyl    chloride, phosgene or chloroformic esters,    (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6,    341-5, 1968)    or when acylamino acids of the formula (XVIII)

in whichA, Q¹, Q², m, W, X, Y and Z have the meanings given above,are esterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XVIII)

in whichA, Q¹, Q², m, W, X, Y and Z have the meanings given above,are novel.

The compounds of the formula (XVIII) are obtained, for example, when1-aminocyclohexane-carboxylic acids of the formula (XIX)

in whichA, m, Q¹ and Q² have the meanings mentioned aboveare acylated with substituted phenylacetic acid derivatives of theformula (XVII)

in whichU, W, X, Y and Z have the meanings given above andfor example following the method of Schotten-Baumann (Organikum [OrganicChemistry], VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p.505).

Some of the compounds of the formula (XVII) are known, and/or can beprepared by the known processes of the laid-open patents cited at theoutset.

The compounds of the formulae (XVI) and (XIX) are novel and can beprepared by known processes (see, for example, Compagnon, Ann. Chim.(Paris) [14] 5, p. 11-22, 23-27 (1970), L. Munday, J. Chem. Soc. 4372(1961); J. T. Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975)).

The novel 1-aminocyclohexanecarboxylic acids (XIX) are generallyobtainable by the Bucherer-Bergs synthesis or by the Strecker synthesisand are in each case obtained in different isomer forms. For the sake ofsimplicity, hereinbelow the isomers in which the radical A in the4-position and the amino group are positioned equatorial/axial oraxial/equatorial are referred to as β. For the sake of simplicity,hereinbelow the isomers in which the amino group and the radical A inthe 4-position are equatorial/equatorial or axial/axial are referred toas α.

(L. Munday, J. Chem. Soc. 4372 (1961)).

The compounds of the formula (XIX) are obtained, for example, byreacting compounds of the formula (XXIII)

in which A has the meanings given above. Some of the compounds of theformula (XXIII) are novel, and can be prepared by known processes of thelaid-open patents cited at the outset.

Furthermore, the starting materials of the formula (II), used in theabove process (A),

in whichA, Q¹, Q², m, W, X, Y, Z and R⁸ have the meanings given above,can be prepared by reacting 1-aminocyclohexanecarbonitriles of theformula (XX)

in whichA, m, Q¹ and Q² have the meanings given above,with substituted phenylacetic acid derivatives of the formula (XVII)

in whichU, W, X, Y and Z have the meanings given above,to give compounds of the formula (XXI)

in whichA, m, Q¹, Q², W, X, Y and Z have the meanings given above,and subsequently subjecting the latter to acid alcoholysis.

The compounds of the formula (XXI) are likewise novel. Some of thecompounds of the formula (XX) are novel, and can be prepared, forexample, as described in EP-A-595 130.

The compounds of the formula (III)

in whichA, m, Q¹, Q², W, X, Y, Z and R⁸ have the meanings given above,are novel.

They can be prepared in a simple manner by methods known in principle.

The compounds of the formula (III), for example, are obtained when

1-hydroxycyclohexanecarboxylic esters of the formula (XXII)

in whichA, m, Q¹, Q² and R⁸ have the meanings given above,are acylated with substituted phenylacetic acid derivatives of theformula (XVII)

in whichU, W, X, Y and Z have the meanings given above,(Chem. Reviews 52, 237-416 (1953)).

The 1-hydroxyhaloalkoxycyclohexylcarboxylic esters of the formula (XXII)are novel. They are obtained, for example, when substituted1-hydroxyhaloalkoxycyclohexanecarbonitriles are reacted in the presenceof acids, for example according to Pinner, with alcohols. Thecyanohydrin is obtained, for example, by reaction of substitutedhaloalkoxycyclohexan-1-ones with hydrocyanic acid (see WO 99/16748).

The acyl halides of the formula (IV), carboxylic anhydrides of theformula (V), chloroformic esters or chloroformic thioesters of theformula (VI), chloromonothioformic esters or chlorodithioformic estersof the formula (VII), sulfonyl chlorides of the formula (VIII),phosphorus compounds of the formula (IX) and metal hydroxides, metalalkoxides or amines of the formulae (X) and (XI) and isocyanates of theformula (XII) and carbamoyl chlorides of the formula (XIII) and boronicacids of the formula (XV) furthermore required as starting materials forcarrying out the processes (C), (D), (E), (F), (G), (H), (I) and (J)according to the invention are generally known compounds from organicand inorganic chemistry.

In addition, the compounds of the formulae (XVII), (I-1-a′-I-2-g′) and(I-1-a″-I-2-g″) are known from the patent applications cited at theoutset, and/or they can be prepared by the methods given in thesepublications.

The process (A) is characterized in that compounds of the formula (II)in which A, Q¹, Q², m, W, X, Y, Z and R⁸ have the meanings given aboveare subjected to an intramolecular condensation in the presence of adiluent and in the presence of a base.

Suitable diluents for the process (A) according to the invention are allorganic solvents which are inert to the reaction participants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide andN-methylpyrrolidone, and also alcohols, such as methanol, ethanol,propanol, isopropanol, butanol, isobutanol and tert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (A) according to the invention are all customary protonacceptors. The following can preferably be used: the oxides, hydroxidesand carbonates of alkali metals and alkaline earth metals, such assodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide,sodium carbonate, potassium carbonate and calcium carbonate, all ofwhich can also be employed in the presence of phase-transfer catalystssuch as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈-C₁₀)ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine). Alkali metalssuch as sodium or potassium can furthermore be used. Furthermore, alkalimetal and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and additionally also alkalimetal alkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide can be employed.

When carrying out the process (A) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −75° C. and200° C., preferably between −50° C. and 150° C.

Process (A) according to the invention is generally carried out underatmospheric pressure.

When carrying out the process (A) according to the invention, thereaction component of the formula (II) and the deprotonating base aregenerally employed in equimolar to approximately double-equimolaramounts. However, it is possible to use one or the other reactants in alarger excess (up to 3 mol).

Suitable diluents for the process (B) according to the invention are allorganic solvents which are inert to the reaction participants.Preference is given to using hydrocarbons, such as toluene and xylene,furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide andN-methyl-pyrrolidone. It is also possible to employ alcohols, such asmethanol, ethanol, propanol, isopropanol, butanol, isobutanol andtert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (B) according to the invention are all customary protonacceptors. The following can preferably be used: the oxides, hydroxidesand carbonates of alkali metals and alkaline earth metals, such assodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide,sodium carbonate, potassium carbonate and calcium carbonate, all ofwhich can also be employed in the presence of phase-transfer catalystssuch as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈-C₁₀)ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine). Alkali metalssuch as sodium or potassium can furthermore be used. Furthermore, alkalimetal and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and additionally also alkalimetal alkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide can be employed.

When carrying out the process (B) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −75° C. and200° C., preferably between −50° C. and 150° C.

Process (B) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (B) according to the invention, the reactantsof the formula (II) and the deprotonating bases are generally employedin approximately twice the equimolar amounts. However, it is possible touse either reactant in a larger excess (up to 3 mol).

The process (C_(α)) is characterized in that compounds of the formulae(I-1-a) to (I-2-a) are in each case reacted with carbonyl halides of theformula (IV), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Suitable diluents for the process (C_(α)) according to the invention areall solvents which are inert to the acyl halides. Preference is given tousing hydrocarbons, such as benzine, benzene, toluene, xylene andtetraline, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such asdimethylformamide, dimethyl sulfoxide and sulfolane. If the acid halideis sufficiently stable to hydrolysis, the reaction may also be carriedout in the presence of water.

Suitable acid binders for the reaction according to the process (C_(α))according to the invention are all customary acid acceptors. Thefollowing can preferably be used: tertiary amines such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig Base and N,N-dimethyl-anilin,furthermore alkali metal oxides such as magnesium oxide and calciumoxide, moreover alkali metal carbonates and alkaline earth metalcarbonates such as sodium carbonate, potassium carbonate and calciumcarbonate, and alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide.

The reaction temperature in the process (C_(α)) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C_(α)) according to the invention, thestarting materials of the formulae (I-1-a) to (I-2-a) and the carbonylhalide of the formula (IV) are generally in each case employed inapproximately equivalent amounts. However, it is also possible to employthe carboxylic acid halides in a larger excess (of up to 5 mol). Work-upis carried out by customary methods.

The process (C_(β)) is characterized in that compounds of the formulae(I-1-a) to (I-2-a) are in each case reacted with carboxylic anhydridesof the formula (V), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Preferred diluents for the process (C_(β)) according to the inventionare those diluents which are also preferred when acyl halides are used.Besides, a carboxylic anhydride used in excess may also simultaneouslyact as the diluent.

In the process (C_(β)), acid binders which are added, if appropriate,are preferably those acid binders which are also preferred when acylhalides are used.

In the process (C_(β)) according to the invention, the reactiontemperature can be varied within a relatively wide range. In general,the process is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C_(β)) according to the invention, thestarting materials of the formulae (I-1-a) to (I-2-a) and the carboxylicanhydride of the formula (V) are generally each employed inapproximately equivalent amounts. However, it is also possible to employthe carboxylic anhydride in a larger excess (of up to 5 mol). Work-up iscarried out by customary methods.

In general, a procedure is followed in which diluent, excess carboxylicanhydride and the carboxylic acid which forms are removed bydistillation or by washing with an organic solvent or with water.

Process (D) is characterized in that compounds of the formulae (I-1-a)to (I-2-a) are reacted in each case with chloroformic esters orchloroformic thioesters of the formula (VI), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

Suitable acid binders for the process (D) according to the invention areall customary acid acceptors. Preference is given to using tertiaryamines, such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such asmagnesium oxide and calcium oxide, moreover alkali metal and alkalineearth metal carbonates, such as sodium carbonate, potassium carbonateand calcium carbonate, and also alkali metal hydroxides, such as sodiumhydroxide and potassium hydroxide.

Diluents which can be employed in process (D) according to the inventionare all solvents which are inert to the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzine, benzene, toluene, xylene and tetraline, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, moreover nitriles, such as acetonitrile,and also strongly polar solvents, such as dimethylformamide, dimethylsulfoxide and sulfolane.

When carrying out the process (D) according to the invention, thereaction temperature can be varied within a relatively wide range. Thereaction temperature is generally between −20° C. and +100° C.,preferably between 0° C. and 50° C.

Process (D) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (D) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-2-a) and the correspondingchloroformic ester or chloroformic thioester of the formula (VI) aregenerally used in each case in approximately equivalent amounts.However, it is also possible to employ one or the other reactant in alarger excess (of up to 2 mol). Work-up is carried out by customarymethods. In general, a procedure is followed in which the salts whichhave precipitated are removed and the reaction mixture which remains isconcentrated by stripping off the diluent.

Process (E) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith compounds of the formula (VII) in the presence of a diluent and, ifappropriate, in the presence of an acid binder.

In preparation process (E), approximately 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (VII) is reacted atfrom 0 to 120° C., preferably at from 20 to 60° C., per mole of startingcompound of the formulae (I-1-a) to (I-2-a).

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulfones, sulfoxides, but alsohaloalkanes.

Preference is given to using dimethyl sulfoxide, tetrahydrofuran,dimethylformamide, ethyl acetate or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-2-a) by addition of strong deprotonating agents such as, forexample, sodium hydride or potassium tertiary-butylate, the furtheraddition of acid binders can be dispensed with.

Suitable bases for the process (E) are all customary proton acceptors.Preference is given to using alkali metal hydrides, alkali metalalkoxides, alkali metal or alkaline earth metal carbonates orbicarbonates or nitrogen bases. Examples which may be mentioned aresodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide,potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine,diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO),diazabicyclononene (DBN) and diazabicycloundecene (DBU).

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods.

Process (F) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith sulfonyl chloride of the formula (VIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In preparation process (F), about 1 mol of sulfonyl chloride of theformula (VIII) is reacted per mole of starting material of the formulae(I-1-a) to (I-2-a), at from −20 to 150° C., preferably at from 0 to 70°C.

The process (F) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents, such as ethers,amides, ketones, carboxylic esters, nitriles, sulfones, sulfoxides orhalogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulfoxide, tetrahydrofuran,dimethylformamide, ethyl acetate or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-2-a) is synthesized by addition of strong deprotonating agents(such as, for example, sodium hydride or potassium tertiary-butoxide),the further addition of acid binders can be dispensed with.

If acid binders are employed, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods.

Process (G) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith phosphorus compounds of the formula (IX), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In preparation process (G), 1 to 2, preferably 1 to 1.3, mole of thephosphorus compound of the formula (IX) are reacted at temperatures ofbetween −40° C. and 150° C., preferably between −10 and 110° C., permole of the compounds (I-1-a) to (I-2-a) in order to obtain compounds ofthe formulae (I-1-e) to (I-2-e).

The process (G) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents, such as ethers,carboxylic esters, halogenated hydrocarbons, ketones, amides, nitriles,sulfones, sulfoxides, etc.

Substances which are preferably employed are acetonitrile, dimethylsulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid binders which are optionally added are customary inorganicor organic bases such as hydroxides, carbonates or amines. Examplesinclude sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods of organic chemistry. The end productsare preferably purified by crystallization, chromatographic purificationor “incipient distillation”, i.e. removal of the volatile componentsunder reduced pressure.

The process (H) is characterized in that compounds of the formulae(I-1-a) to (I-2-a) are in each case reacted with metal hydroxides ormetal alkoxides of the formula (X) or amines of the formula (XI), ifappropriate in the presence of a dilluent.

Preferred diluents for the process (H) according to the invention areethers, such as tetrahydrofuran, dioxane, diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.Process (H) according to the invention is generally carried out underatmospheric pressure. The reaction temperature is generally between −20°C. and 100° C., preferably between 0° C. and 50° C.

The process (I) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are in each case reactedwith (Iα) compounds of the formula (XII), if appropriate in the presenceof a diluent and if appropriate in the presence of a catalyst, or (Iβ)with compounds of the formula (XIII), if appropriate in the presence ofa diluent and if appropriate in the presence of an acid binder.

In the preparation process (Iα), approximately 1 mol of isocyanate ofthe formula (XII) is reacted per mole of starting material of theformulae (I-1-a) to (I-2-a), at from 0 to 100° C., preferably at from 20to 50° C.

The process (Iα) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert organic solvents, such as aromatichydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles,sulfones or sulfoxides.

If appropriate, catalysts may be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds such as, for example, dibutyltin dilaurate.

The process is preferably carried out under atmospheric pressure.

In the preparation process (Iβ), approximately 1 mol of carbamoylchloride of the formula (XIII) is reacted per mole of starting materialof the formulae (I-1-a) to (I-2-a), at from 0 to 150° C., preferably atfrom 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, carboxylic esters, nitriles, ketones,amides, sulfones, sulfoxides or halogenated hydrocarbons.

Preference is given to using dimethyl sulfoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-1-a)to (I-2-a) is synthesized by adding strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butoxide), thefurther addition of acid binders can be dispensed with.

If acid binders are employed, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate triethylamine or pyridine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods.

Suitable catalysts for carrying out the processes (Jα) and (Jβ)according to the invention are palladium(0) complexes. Preference isgiven, for example, to tetrakis(triphenylphosphine)palladium. Ifappropriate, it is also possible to use palladium(II) compounds, forexample PdCl₂, Pd(OAc)₂. If palladium(II) compounds are used,phosphines, such as, for example, tricyclohexylphosphine, are generallyemployed as complex formers.

Suitable acid acceptors for carrying out the processes (Jα) and (Jβ)according to the invention are inorganic or organic bases. Thesepreferably include alkaline earth metal or alkali metal hydroxides,acetates, carbonates or bicarbonates, such as, for example, sodiumhydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide,sodium acetate, potassium acetate, calcium acetate or ammonium acetate,sodium carbonate, potassium carbonate, cesium carbonate or ammoniumcarbonate, sodium bicarbonate or potassium bicarbonate, alkali metalfluorides, such as, for example, cesium fluoride, alkali metalphosphates, such as, for example, potassium dihydrogen phosphate,potassium phosphate and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out the processes (Jα) and (Jβ) accordingto the invention are water, organic solvents and any mixtures thereof.There may be mentioned by way of example: aliphatic, alicyclic oraromatic hydrocarbons, such as, for example, petroleum ether, hexane,heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene ordecalin; halogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride,dichloroethane, trichloroethane or tetrachloroethylene; ethers, such asdiethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole;alcohols, such as methanol, ethanol, n- or isopropanol, n-, iso-, sec-or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonomethyl ether; water.

In the processes (Jα) and (Jβ) according to the invention, the reactiontemperature can be varied within a relatively wide range. In general,the process is carried out at temperatures between 0° C. and +140° C.,preferably between 50° C. and +100° C.

When carrying out the processes (Jα) and (Jβ) according to theinvention, the boronic acids of the formulae (XVα) and (XVβ) in which Yand Z have the meaning given above and compounds of the formulae(I-1-a′) to (I-2-g′) in which A, D, G, Q¹, Q², W, X, Y and Z′ have themeaning given above and the compounds of the formulae (I-1-a″) to(I-2-g″) in which A, D, G, Q¹, Q², m, W, X, Z and Y′ have the meaninggiven above are employed in a molar ratio of from 1:1 to 3:1, preferablyof from 1:1 to 2:1. In general, from 0.005 to 0.5 mol, preferably from0.01 mol to 0.1 mol, of catalyst are employed per mole of the compoundsof the formulae (I-1-a′) to (I-2-g′) or (I-1-a″) to (I-2-g″). The baseis generally employed in excess. Work-up is carried out by customarymethods.

The active compounds according to the invention, in combination withgood plant tolerance, favourable toxicity to warm-blooded animals andbeing tolerated well by the environment, are suitable for protectingplants and plant organs, for increasing harvest yields, for improvingthe quality of harvested material and for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inforests, in gardens and leisure facilities, in the protection of storedproducts and of materials, and in the hygiene sector. They may bepreferably employed as plant protection agents. They are active againstnormally sensitive and resistant species and against all or some stagesof development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus siro, Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp.,Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp.,Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri,Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp.,Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychusspp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Coleoptera, for example, Acanthoscelides obtectus,Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp.,Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus,Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp.,Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchuslapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinuscubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans,Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosternaconsanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus,Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha,Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptushololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchussulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp.,Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinusspp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp.,Sphenophorus spp., Steprnechus spp., Symphyletes spp., Tenebrio molitor,Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrusspp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp.,Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fanniaspp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp.,Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp.,Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanusspp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp.,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control Protozoa, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis,Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistusspp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisaspp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae,Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp.,Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergellasingularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatomaspp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobusbarodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui,Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis,Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani,Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicorynebrassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacunalanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii,Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp.,Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp.,Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterusarundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi,Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari,Metcalfiella spp., Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettixspp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga,Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.,Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodonhumuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp.,Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcusspp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp.,Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp.,Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus,Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina,Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp.,Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp.,Unaspis spp., Viteus vitifolii.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonic and Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus and Porcellio scaber.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major, Aedialeucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathrabrassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana,Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo spp.,Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Eariasinsulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp.,Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella,Laphygma spp., Lithocolletis blancardella, Lithophane antennata,Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestrabrassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae,Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella,Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp.,Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Theimesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana,Trichoplusia spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae,Locusta spp., Melanoplus spp., Periplaneta americana, Schistocercagregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp. andXenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanoptera, for example, Baliothrips biformis,Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothripsfemoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothripsspp., Taeniothrips cardamoni, Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The phytoparasitic nematodes include, for example, Anguina spp.,Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchusdipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp.,Tylenchulus spp., Tylenchulus semipenetrans and Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(mycoplasma-like organisms) and RLO (Rickettsia-like organisms). Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant varieties which can or cannot be protected by varietal propertyrights. Plant parts are to be understood as meaning all above-ground andbelow-ground parts and organs of plants, such as shoot, leaf, flower androot, examples which may be mentioned being leaves, needles, stems,trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubersand rhizomes. The plant parts also include harvested material and alsovegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seed.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injecting, and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspoemulsion concentrates, natural compoundsimpregnated with active compound, synthetic substances impregnated withactive compound, fertilizers and also microencapsulations in polymericsubstances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that is to sayemulsifiers and/or dispersants, and/or foam-formers. The formulationsare prepared either in suitable plants or else before or duringapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfonesand sulfoxides (such as dimethyl sulfoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulfoxide, and also water.

Suitable Solid Carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic materials such as highly-disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite, dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, corn cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulfonates, alkyl sulfates, arylsulfonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or -POP ethers, acidand/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POPPOE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan or -sugar adducts, alkyl or aryl sulfates, alkyl- orarylsulfonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulfonic acidderivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulfonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

The formulations generally comprise between 0.01 and 98% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use foams, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances, herbicides,safeners, fertilizers or semiochemicals.

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergists are compounds whichincrease the action of the active compounds, without it being necessaryfor the synergist added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the environment of the plant, on the surface ofplant parts or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.00000001 to95% by weight of active compound, preferably between 0.00001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The terms “parts”and “parts of plants” or “plant parts” have been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus possible are, for example, reducedapplication rates and/or a widening of the activity spectrum and/or anincrease of the activity of the compounds and compositions which can beused according to the invention, better plant growth, increasedtolerance to high or low temperatures, increased tolerance to drought orto water or soil salt content, increased flowering, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/orhigher nutrient value of the harvested products, increased storabilityand/or processibility of the harvested products, which exceed theeffects normally to be expected.

The transgenic plants or plant cultivars (i.e. those obtained bygenetical engineering) which are preferably treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenseof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), corn, soybeans,potatoes, sugar beets, tomatoes, peas and other types of vegetable,cotton, tobacco, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), with particular emphasis beinggiven to corn, soybeans, potatoes, cotton, tobacco and oilseed rape.Traits that are emphasized in particular are increased defense of theplants against insects, arachnids, nematodes and molluscs by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulfonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned arecorn varieties, cotton varieties, soybean varieties and potato varietieswhich are sold under the trade names YIELD GARD® (for example corn,cotton, soybeans), KnockOut® (for example corn), StarLink® (for examplecorn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).Examples of herbicide-tolerant plants which may be mentioned are cornvarieties, cotton varieties and soybean varieties which are sold underthe trade names Roundup Ready® (tolerance to glyphosate, for examplecorn, cotton, soybean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulfonylureas, for example corn). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example corn). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plants will be developed and/or marketed in thefuture.

The plants stated can be treated particularly advantageously inaccordance with the invention with the compounds of the general formulaI or the active compound mixtures according to the invention. Thepreferred ranges stated above for the active compounds or mixtures alsoapply to the treatment of these plants. Particular emphasis is given tothe treatment of plants with the compounds or mixtures specificallymentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ecto- and endoparasites), suchas hard ticks, soft ticks, mange mites, leaf mites, flies (biting andlicking), parasitic fly larvae, lice, hair lice, feather lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acari (Acarina) and the orders of the Meta- andMesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector and in animal husbandry in a known manner by enteraladministration in the form of, for example, tablets, capsules, potions,drenches, granules, pastes, boluses, the feed-through process andsuppositories, by parenteral administration, such as, for example, byinjection (intramuscular, subcutaneous, intravenous, intraperitoneal andthe like), implants, by nasal administration, by dermal use in the form,for example, of dipping or bathing, spraying, pouring on and spottingon, washing, powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive compounds of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) comprising the active compoundsin an amount of from 1 to 80% by weight, either directly or after 100 to10 000-fold dilution, or they may be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention also have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec., Dinoderus minutus;

Dermapterans, such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur;

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticuliteimes lucifugus, Mastoteiiues darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus;

Bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

With respect to additional partners for mixing, reference is made to theinsecticides and fungicides mentioned above.

The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Furthermore, the compounds according to the invention can be used aloneor in combinations with other active compounds as antifoulingcompositions.

The active compounds are also suitable for controlling animal pests inthe domestic field, in hygiene and in the protection of stored products,in particular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active compounds and auxiliaries in domestic insecticide productsfor controlling these pests. They are active against sensitive andresistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleoptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix,Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, neonicotinoids, growth regulatorsor active compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orplastic, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Equally, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, ornamental tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns and turf andpastures and for selective weed control in annual crops.

The according to the invention have strong herbicidal activity and abroad active spectrum when used on the soil and on above-ground plantparts. To a certain extent they are also suitable for the selectivecontrol of monocotyledonous and dicotyledonous weeds in monocotyledonousand dicotyledonous crops, both by the pre-emergence and by thepost-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is to say,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulfoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as highly-disperse silica, alumina and silicates;suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and also synthetic granules of inorganic and organic meals,and granules of organic material such as sawdust, coconut shells, corncobs and tobacco stalks; suitable emulsifiers and/or foam formers are:for example nonionic and anionic emulsifiers such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates,arylsulfonates, or else protein hydrolysates; suitable dispersants are:for example lignosulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds or active compound combinations can be used assuch, in the form of their formulations or in the use forms preparedtherefrom by further dilution, such as ready-to-use solutions,suspensions, emulsions, powders, pastes and granules. They are used in acustomary manner, for example by watering, spraying, atomizing orbroadcasting.

The active compounds or active compound combinations according to theinvention can be applied both before and after emergence of the plants.They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The advantageous effect of the compatibility with crop plants of theactive compound combinations according to the invention is particularlypronounced at certain concentration ratios. However, the weight ratiosof the active compounds in the active compound combinations can bevaried within relatively wide ranges. In general, from 0.001 to 1000parts by weight, preferably from 0.01 to 100 parts by weight,particularly preferably 0.05 to 20 parts by weight, of one of thecompounds which improves crop plant compatibility (antidotes/safeners)mentioned above under (b′) are present per part by weight of activecompound of the formula (I).

The active compound combinations according to the invention aregenerally applied in the form of finished formulations. However, theactive compounds contained in the active compound combinations can, asindividual formulations, also be mixed during use, i.e. be applied inthe form of tank mixes.

For certain applications, in particular in the post-emergence method, itmay furthermore be advantageous to include, as further additives in theformulations, mineral or vegetable oils which are tolerated by plants(for example the commercial preparation “Rako Binol”), or ammoniumsalts, such as, for example, ammonium sulfate or ammonium thiocyanate.

The novel active compound combinations can be used as such, in the formof their formulations or in the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. They are used in a customary manner, forexample by watering, spraying, atomizing, dusting or broadcasting.

The application rates of the active compound combinations according tothe invention can be varied within a certain range; they depend, interalia, on the weather and on soil factors. In general, the applicationrates are between 0.001 and 5 kg per ha, preferably between 0.005 and 2kg per ha, particularly preferably between 0.01 and 0.5 kg per ha.

The active compound combinations according to the invention can beapplied before and after emergence of the plants, that is to say by thepre-emergence and post-emergence method.

Depending on their properties, the safeners to be used according to theinvention can be used for pretreating the seed of the crop plant (seeddressing) or can be introduced into the seed furrows prior to sowing orbe used separately prior to the herbicide or together with theherbicide, before or after emergence of the plants.

Examples of plants which may be mentioned are important crop plants,such as cereals (wheat, barley, rice), corn, soybeans, potatoes, cotton,oilseed rape, beet, sugar cane and also fruit plants (with the fruitsapples, pears, citrus fruits and grapevines), greater emphasis beinggiven to cereals, corn, soybeans, potatoes, cotton and oilseed rape.

The term “active compounds” always also includes the active compoundcombinations mentioned here.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example I-1-a-1

Under argon, 2.98 g of potassium tert-butoxide (95%) are initiallycharged in 10 ml of dimethylacetamide. At 40° C., 4.4 g of the compoundof Example II-1 in 10 ml dimethylacetamide are added dropwise. Themixture is stirred at 40° C. for 4 h. After the reaction has ended(monitored by TLC) the mixture is stirred into 400 ml of ice-water,adjusted to pH 2 using cone. HCl and filtered off with suction. This isfollowed by purification by column chromatography on silica gel(methylene chloride/ethyl acetate 3:1).

Yield: 1.4 g (34% of theory), m.p. 262° C.

The following compounds of the formula (I-1-a) where Q¹ and Q²=H and m=1are obtained analogously to Example (I-1-a-1) and following the generalpreparation instructions

(I-1-a)

Ex. No. W X Y Z A M.p. ° C. Isomer I-1-a-2 C₂H₅ Br CH₃ H —O—CH₂—CF₃ 128α:β 2:7 I-1-a-3 CH₃ CH₃ H 4-F-Ph —O—CH₂—CF₃ 280 β I-1-a-4 C₂H₅ OCH₃ Cl H—O—CH₂—CF₃ 189 α:β 1:2 I-1-a-5 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ 203 α:β 5:9I-1-a-6 CH₃ CH₃ H 4-F-Ph —O—CH₂—CF₃ 260 α I-1-a-7 C₂H₅ Br CH₃ H—O—CH₂—CF₃ 111 α I-1-a-8 H CH₃ Cl H —O—CH₂-CF₃ 210 α:β about 1:9 I-1-a-9CH₃ CH₃ Br H —O—CH₂—CF₃ 269 β I-1-a-10 H CH₃ H H —O—CH₂—CF₃ 217 α:βabout 1:7.5 I-1-a-11 H CH₃ H CH₃ —O—CH₂—CF₃ 212 β I-1-a-12 C₂H₅ C₂H₅ CH₃H —O—CH₂—CF₃ 174 β I-1-a-13 C₂H₅ CH₃ CH₃ H —O—CH₂—CF₃ 176 β I-1-a-14C₂H₅ O—C₂H₅ Cl H —O—CH₂—CF₃ 169 β I-1-a-15 C₂H₅ O—C₂H₅ Cl H —O—CH₂—CF₃106 α I-1-a-16 CH₃ CH₃ CH₃ CH₃ —O—CH₂—CF₃ 254 β I-1-a-17 CH₃ CH₃ CH₃ CH₃—O—CH₂—CF₃ 243 α I-1-a-18 H Cl H 4-Cl-Ph —O—CH₂—CF₃ 247 α I-1-a-19 H ClH 4-Cl-Ph —O—CH₂—CF₃ 226 β I-1-a-20 H Cl H 4-F-Ph —O—CH₂—CF₃ 247 αI-1-a-21 H Cl H 4-F-Ph —O—CH₂—CF₃ >300  β I-1-a-22 CH₃ OCH₃ Cl H—O—CH₂—CF₃ 167 β I-1-a-23 CH₃ OCH₃ Cl H —O—CH₂—CF₃ wax α I-1-a-24 CH₃CH₃ H 4-Cl-Ph —O—CH₂—CF₃ 273 α I-1-a-25 CH₃ CH₃ H 4-Cl-Ph —O—CH₂—CF₃ 288β I-1-a-26 H CH₃ CH₃ CH₃ —O—CH₂—CF₃ 126 α I-1-a-27 H CH₃ CH₃ CH₃—O—CH₂—CF₃ 220 β I-1-a-28 CH₃ CH₃ Cl H —O—CH₂—CF₂—CF₃ * α I-1-a-29 CH₃CH₃ Cl H —O—CH₂—CF₂—CF₃ 202 β I-1-a-30 CH₃ CH₃

H —O—CH₂—CF₃ 281 β I-1-a-31 H CH₃ H 4-F-Ph —O—CH₂—CF₃ 140 α + β about1:2 I-1-a-32 H CH₃ H CH₃ —O—CH₂—CF₂—CF₃ 200 β ¹H-NMR (400 MHz, d₆-DMSO):δ = 1.21-1.24 (dm, 2H, CH₂), 2.08 (s, 6H, Ar—CH ₃), 3.75

Example I-1-b-1

β-isomer

Under argon, 0.4 g of the compound of Example I-1-a-1 (0.001 mol) isinitially charged in 20 ml of ethyl acetate (anhydrous) and 0.1 g oftriethylamine (0.14 ml). 10 mg of Steglich base are used as catalyst;0.11 g of isobutyryl chloride (0.001 mol) in 3 ml of ethyl acetate(anhydrous) is added dropwise at 70° C. The mixture is stirred at 70° C.for 1 h. After concentration, the product is purified by columnchromatography on silica gel (dichloromethane: ethyl acetate=10:1)

Yield: 0.25 g (52% of theory), m.p. 219° C.

The following compounds of the formula (I-1-b) where Q¹ and Q²=H and m=1are obtained analogously to Example (I-1-b-1) and following the generalpreparation instructions

(I-1-b)

Ex. m.p. Iso- No. W X Y Z A R¹ ° C. mer I-1- b-2 CH₃ CH₃ H 4-F-PhO—CH₂—CF₃ i-C₃H₇ 210 β I-1- b-3 C₂H₅ OCH₃ Cl H O—CH₂—CF₃ CH₃ 204- 206 β

Example I-1-c-1

β-isomer

Under argon, 0.4 g of the compound of Example I-1-a-1 (0.001 mol) isinitially charged in 20 ml of methylene chloride (anhydrous) and 0.1 gof triethylamine (0.14 ml). 10 mg of Steglich base are used as catalyst;0.1 ml of ethyl chloroformate (0.001 mol) in 3 ml of methylene chloride(anhydrous) is added dropwise at 20° C. The mixture is stirred at 20° C.for 1 h. After concentration, the product is purified by columnchromatography on silica gel (dichloromethane: ethyl acetate=10:1).

Yield: 0.3 g (62.6% of theory), m.p. 174° C.

The following compounds of the formula (I-1-c) where Q¹ and Q²=H and m=1are obtained analogously to Example (I-1-c-1) and following the generalpreparation instructions

Ex. No. W X Y Z A M R² m.p. ° C. Isomer I-1-c-2 CH₃ CH₃ H 4-F-Ph—O—CH₂—CF₃ O CH₃ 196 β I-1-c-3 C₂H₅ Br CH₃ H —O—CH₂—CF₃ O C₂H₅ 204-206 β

Example II-1

Under argon, 3.2 g of the compound of Example XVI-1 are initiallycharged in 30 ml of ethyl acetate. 11 ml of 1N NaOH are added. At 0-5°C., 10 ml of 1N NaOH and 2.17 g of 4-chloro-2,6-dimethylphenylacetylchloride in 10 ml of ethyl acetate are simultaneously added dropwise.The mixture is stirred for another 1 h. The aqueous phase is separatedoff and extracted with methylene chloride. The combined organic phasesare washed with NaHCO₃ solution, dried with magnesium sulfate andconcentrated on a rotary evaporator. Purification is carried out onsilica gel using the mobile phase magnesium sulfate.

Yield: 4.5 g (80% of theory), m.p. 162° C.

The following compounds of the formula (II) where Q¹ and Q²=H and m=1are obtained analogously to Example (II-1) and following the generalpreparation instructions

(II)

Ex. No. W X Y Z A R⁸ M.p. ° C. Isomer II-2 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ CH₃160 α + β mixture II-3 CH₃ CH₃ H 4-F-Ph —O—CH₂—CF₃ CH₃ 139 α + β mixtureII-4 C₂H₅ OCH₃ Cl H —O—CH₂—CF₃ CH₃ 136 α + β mixture II-5 C₂H₅ Br 4-CH₃H —O—CH₂—CF₃ CH₃ 138 α + β mixture II-6 H CH₃ H CH₃ —O—CH₂—CF₃ CH₃ 151α + β mixture II-7 H CH₃ Cl H —O—CH₂—CF₃ CH₃ 155 α + β mixture II-8 HCH₃ H H —O—CH₂—CF₃ CH₃ 130 α + β mixture II-9 CH₃ CH₃ Br H —O—CH₂—CF₃CH₃ 174 α + β mixture II-10 CH₃ CH₃ CH₃ H —O—CH₂—CF₂—CF₃ CH₃ 143 α + βmixture II-11 CH₃ C₂H₅ CH₃ H —O—CH₂—CF₃ CH₃ 130 α + β mixture II-12 CH₃OCH₃ Cl H —O—CH₂—CF₃ CH₃ 160 α + β mixture II-13 C₂H₅ C₂H₅ CH₃ H—O—CH₂—CF₃ CH₃ 143 α + β mixture II-14 CH₃ CH₃ CH₃ CH₃ —O—CH₂—CF₃ CH₃165 α + β mixture II-15 C₂H₅ OC₂H₅ Cl H —O—CH₂—CF₃ CH₃ 152 α + β mixtureII-16 CH₃ CH₃

H —O—CH₂—CF₃ CH₃ 135 α + β mixture II-17 H Cl H 4-F-Ph —O—CH₂—CF₃ CH₃131 α + β mixture II-18 H CH₃ H 4-Cl-Ph —O—CH₂—CF₃ CH₃ 152 α + β mixtureII-19 CH₃ CH₃ H 4-Cl-Ph —O—CH₂—CF₃ CH₃ 188 α + β mixture II-20 H Cl H4-Cl-Ph —O—CH₂—CF₃ CH₃ 160 α + β mixture II-21 H CH₃ CH₃ CH₃ —O—CH₂—CF₃CH₃ 153 α + β mixture II-22 CH₃ CH₃ Cl H —O—CH₂—CF₂—CF₃ CH₃ oil α + βmixture II-23 H CH₃ H CH₃ —O—CH₂—CF₂—CF₃ CH₃ oil α + β mixture II-24 HCH₃ H 4-F-Ph —O—CH₂—CF₃ CH₃ 116 α + β mixture II-25 C₂H₅ Br CH₃ H—O—CH₂—CF₂—CF₃ CH₃ 116 α + β mixture

Example XVI-1

Under argon, 43 g of the compound of Example XIX-1 are initially chargedin 500 ml of methanol, and 15 ml (0.205 mol) of thionyl chloride areslowly added dropwise at 0-5° C. The mixture is stirred at 0° C. for 30min and then at 40° C. for 24 h. The solution is cooled to 5° C. Theprecipitate is filtered off with suction and the solvent is removed on arotary evaporator. The residue is triturated with methyl tert-butylether and the precipitate is filtered off with suction. The product isprecipitated from methylene chloride/n-hexane.

Yield starting from 4-trifluoroethoxycyclohexanone: 37 g (=95% oftheory), m.p. 176° C. about 1:2 α+β isomers

The following examples of the formula (XVI) where Q¹ and Q²=H and m=1are obtained analogously to Example XVI-1

(XVI)

¹H-NMR (ppm) (400 MHz, Iso- Ex. No. A R⁸ d₆-DMSO) mer XVI-2O—CH₂—CF₂—CF₃ CH₃ 3.74, 3.75 (s, 3H, OCH ₃) α + β 4.08, 4.15 (tm, 2H,O—CH ₂—CF₂) XVI-3 O—CH₂—CF₂—CHF₂ CH₃ 3.75, 3.76 (s, 3H, OCH ₃) 3.87-3.95(tm, 2H, O—CH₂—CF₂) 6.27-6.73 (qm, 1, CF₂—CHF₂) α + β

Example XIX-1

Under argon, 41.5 g of the compound of Example XXIII-1 are suspended in250 ml of 30% strength KOH. The mixture is stirred under reflux(nitrogen) for 24 h. The mixture is concentrated to about 25% of itsoriginal volume, at 0-10° C. adjusted to pH 5 using conc. HCl, the wateris removed using a rotary evaporator and the precipitate is dried. Thecrude product is reacted without additional purification.

The following compounds of the formula (XIX) where Q¹ and Q²=H and m=1are obtained analogously to Example XIX-1

(XIX)

Ex. No. A XIX-2 O—CH₂—CF₂—CF₃ XIX-3 O—CH₂—CF₂—CHF₂

Example XXIII-1

270 ml of water, 64 g (0.666 mol) of ammonium carbonate and 7.15 g(0.146 mol) of sodium cyanide are initially charged under argon. 26 g(0.1325 mol) of 4-trifluoroethoxycyclohexanone are added dropwise at 20°C. The reaction mixture is stirred at 55° C. to 60° C. for 24 h, then at0° C. to 5° C. for 2 h. The solid is filtered off with suction, washedwith the mother liquor and dried. The crude product is reacted withoutadditional purification.

The following compounds of the formula (XXIII) where Q¹ and Q²=H and m=1are obtained analogously to Example XXIII-1

(XXIII)

¹H-NMR (ppm) Iso- Ex. No. A (400 MHz, d₆-DMSO) mer XXIII-2 O—CH₂—CF₂—CF₃

4.03-4.14 (qm, 2H, OCH₂—CF₂) α + β XXIII-3 O—CH₂—CF₂—CHF₂

3.85-3.96 (qm, 2H, O—CH ₂—CF₂) 6.24-6.54 (tm, 1H, CF₂—CHF₂) 8.12, 8.17(2sb, 1H, NH) α + β 1:2

Preparation of 4-trifluoroethoxycyclohexanone Step 1

Under nitrogen, 53 g (0.276 mol) of 4-trifluoroethoxyphenol areinitially charged in 420 ml of methylcyclohexane, and 0.3 g (0.8 mmol)of borax and the catalyst (5% Pd/C, 6 g) are added. A hydrogen pressureof 50 bar is applied, and the reaction mixture is heated to 160° C. Thehydrogen pressure is then increased to 100 bar, and hydrogenation iscontinued until nearly all of the starting material has been converted.After emptying, the autoclave is carefully rinsed with dichloromethane,the combined organic phases are filtered through Celite 545 and thefilter cake is washed with 500 ml of dichloromethane. The filtrate isconcentrated at a water bath temperature of at most 40° C. and 78 mbar.

Yield: This gives 51 g of a light-pink liquid comprising about 31%4-trifluoroethoxycyclohexanone, about 51% of4-trifluoroethoxycyclohexanol and about 14% of methylcyclohexane.Without further purification, the crude product is oxidized withpyridinium dichromate.

Step 2

100 g of molecular sieves and 105.25 g (0.28 mol) of finely powderedpyridinium dichromate are suspended in 450 ml of dichloromethane, and 51g of the mixture from step 1 in about 50 ml of dichloromethane are addeddropwise. With monitoring by gas chromatography, the reaction mixture isstirred at room temperature for 18 h. After the reaction has ended, (550ml) of diethyl ether is added and the mixture is filtered throughCelite. The filter cake is washed with diethyl ether. The filtrate iswashed with 1N HCl (3×250 ml), water (200 ml) and saturated NaClsolution (200 ml) and dried. The solvent is carefully removed at 35° C.and 60 mbar. The residue is distilled under reduced pressure.

Yield: 24 g (b.p.₁₇ 102-104° C.)

Example (I-2-a-1)

1.081 g (4 mmol) of ethyl4-trifluoroethoxy-1-hydroxycyclohexanecarboxylate (XXII-1) and 0.899 g(4 mmol) of 2,6-diethyl-4-methylphenylacetyl chloride are heated at 120°C. for 8 h, cooled, divided between methyl tert-butyl ether (MTBE) and5% strength aqueous sodium hydroxide solution, the phases are separated,and the organic phase is dried and concentrated on a rotary evaporator.This gives 1.6 g of product which is initially charged in 30 ml ofN,N-dimethylformamide, 0.59 g of potassium tert-butoxide are added andthe mixture is stirred at room temperature overnight. The reactionmixture is stirred into water and extracted with MTBE, the aqueous phaseis acidified with hydrochloric acid and extracted with methylenechloride and the extract is dried and concentrated on a rotaryevaporator.

Yield: 1.4 g (=92% of theory) isomer mixture α+β about 1:1, log P α3.78; β 3.64

The following compounds of the formula (I-2-a) where Q¹ and Q²=H and m=1are obtained analogously to Example (I-1-a-2) and following the generalpreparation instructions:

(I-2-a)

Ex. No. W X Y Z A log P Isomer I-2-a-2 H CH₃ H CH₃ —O—CH₂—CF₃ α 3.10 β2.95 α + β about 1:1 I-2-a-3 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ α 3.31 β 3.18 α +β about 1:1 I-2-a-4 H CH₃ CH₃ CH₃ —O—CH₂—CF₃ α 3.34 β 3.20 α + β about1:1 I-2-a-5 CH₃ C₂H₅ CH₃ H —O—CH₂—CF₃ α 3.54 β 3.41 α + β about 1:1I-2-a-6 CH₃ CH₃ H 4-Cl-Ph —O—CH₂—CF₃ α 4.29 β 4.13 α + β about 1:1I-2-a-7 H CH₃ H 4-Cl-Ph —O—CH₂—CF₃ α 4.09 α 3.93 α + β about 1:1 I-2-a-8CH₃ CH₃ Cl H —O—CH₂—CF₃ α 3.39 β 3.25 α + β about 1:1 I-2-a-9 CH₃ CH₃CH₃ H —O—CH₂—CF₃ 3.29 α* I-2-a-10 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ 3.16 β*I-2-a-11 CH₃ OCH₃ CH₃ H —O—CH₂—CF₃ α 3.07 β 2.94 α + β about 1:1I-2-a-12 CH₃ C₂H₅ 4-Cl-Ph H —O—CH₂—CF₃ α 4.51 β 4.36 α + β about 1:1*isolated by preparative HPLC

Example (I-2-b-1)

Example (I-2-b-2)

At room temperature, 0.062 g (0.582 mmol) of isobutyryl chloride inmethyl chloride are added to 0.2 g (0.485 mmol) of the compound ofExample (I-2-a-1) and 0.06 g (0.582 mmol) of triethylamine in 10 ml ofmethylene chloride, and the mixture is stirred at room temperatureovernight. The reaction mixture is concentrated and the residue isseparated by preparative HPLC on RP18 silica gel using anacetonitrile/water gradient (0.05% formic acid) 50:50→100:0 over 20 min.

Yield:

59 mg=24% of theory (I-2-b-1), log P 5.69 and 72 mg=30% of theory(I-2-b-2), log P 5.40

The following compounds of the formula (I-2-b) where Q¹ and Q²=H and m=1are obtained analogously to Examples (I-2-b-1) and (I-2-b-2) andfollowing the general preparation instructions:

(I-2-b)

Ex. No. W X Y Z A R¹ log P Isomer I-2-b-3 CH₃ C₂H₅ CH₃ H —O—CH₂—CF₃i-C₃H₇ 5.44 α I-2-b-4 CH₃ C₂H₅ CH₃ H —O—CH₂—CF₃ i-C₃H₇ 5.15 β I-2-b-5 HCH₃ H CH₃ —O—CH₂—CF₃ i-C₃H₇ 4.88 α I-2-b-6 H CH₃ H CH₃ —O—CH₂—CF₃ i-C₃H₇4.62 β I-2-b-7 H CH₃ CH₃ CH₃ —O—CH₂—CF₃ i-C₃H₇ 5.14 α I-2-b-8 H CH₃ CH₃CH₃ —O—CH₂—CF₃ i-C₃H₇ 4.87 β I-2-b-9 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ i-C₃H₇5.14 α I-2-b-10 CH₃ CH₃ CH₃ H —O—CH₂—CF₃ i-C₃H₇ 4.88 β I-2-b-11 CH₃ CH₃H 4-Cl-Ph —O—CH₂—CF₃ i-C₃H₇ 6.11 α I-2-b-12 CH₃ CH₃ H 4-Cl-Ph —O—CH₂—CF₃i-C₃H₇ 5.83 β I-2-b-13 H CH₃ H 4-Cl-Ph —O—CH₂—CF₃ i-C₃H₇ 5.84 α I-2-b-14H CH₃ H 4-Cl-Ph —O—CH₂—CF₃ i-C₃H₇ 5.55 β I-2-b-15 CH₃ CH₃ Cl H—O—CH₂—CF₃ i-C₃H₇ 5.25 α I-2-b-16 CH₃ CH₃ Cl H —O—CH₂—CF₃ i-C₃H₇ 4.97 βI-2-b-17 CH₃ C₂H₅ 4-Cl-Ph H —O—CH₂—CF₃ i-C₃H₇ 6.33 α I-2-b-18 CH₃ C₂H₅4-Cl-Ph H —O—CH₂—CF₃ i-C₃H₇ 6.02 β I-2-b-19 CH₃ OCH₃ CH₃ H —O—CH₂—CF₃i-C₃H₇ 4.72 α I-2-b-20 CH₃ OCH₃ CH₃ H —O—CH₂—CF₃ i-C₃H₇ 4.48 β Ph =phenylDetermination of the logP Values (LC/MS, HCOOH Method):

The logP values given in the tables were determined in accordance withEEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 55°C.

Mobile phases for determination in the acidic range (pH 3.4):

Mobile phase A: acetonitrile+1 ml formic acid/liter. Mobile phase B:water+0.9 ml formic acid/liter. Gradient: from 10% mobile phase A/90%mobile phase B to 95% mobile phase A/5% mobile phase B over 4.25 min.Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones). The lambda max values were determined in themaxima of the chromatographic signals using the UV spectra from 200 nmto 400 nm.

Precursor for Example (XXII-1)1-Hydroxy-4-trifluoroethoxycyclohexanecarbonitrile

13.74 g of sodium cyanide are dissolved in 200 ml of water. Over aperiod of 30 min, 50 g of 4-trifluoroethoxycyclohexanone are then addeddropwise at 20-28° C. with slight cooling. The mixture is stirred at 25°C. for 5 minutes, and 31.48 g of sodium disulfite, dissolved in 100 mlof water, are then added dropwise with cooling at 25-30° C. over aperiod of 30 min. With monitoring by thin-layer chromatography, themixture is stirred at room temperature. The aqueous phase is extracted3× with in each case 90 ml of toluene. The organic phases are combinedand concentrated under reduced pressure.

Yield: 32.52 g

Example (XXII-1)

24 g of 1-hydroxy-4-trifluoroethoxycyclohexanecarbonitrile are dissolvedin 150 ml of ethanol. HCl gas is introduced at −20° C. The cooling bathis allowed to thaw slowly (end at −5° C.), duration of HCl introductionabout 2 h. The mixture is stirred without cooling overnight. Ethanol isdistilled off at 45° C. 150 ml of ice-water are added to the residue,and the mixture is stirred at room temperature for 3 hours. The reactionmixture is extracted 3× with in each case 150 ml of methylene chloride.The combined methylene chloride phases are washed with 200 ml ofsaturated sodium bicarbonate solution and concentrated. Distillation iscarried out under high vacuum using a column (estimated boiling point at8·10⁻² mbar: ˜85° C.).

Yield: 25.6 g

USE EXAMPLES Example No. 1 Phaedon Test Spray Treatment

Solvent: 78.0 parts by weight of acetone  1.5 parts by weight ofdimethylformamide Emulsifier:  0.5 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage (Brassica pekinensis) are sprayed with anactive compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired period of time, the effect in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an effect of ≧80%:

Ex. Nos. I-1-a-1, I-1-b-1, I-2-a-4, I-2-b-6

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an effect of ≧80%:

Ex. Nos. I-1-a-2, I-1-a-3, I-1-a-5, I-1-a-6, I-1-a-7, I-1-a-8, I-1-a-9,I-1-a-12, I-1-a-13, I-1-a-15, I-1-a-16, I-1-a-17, I-1-a-18, I-1-a-19,I-1-a-20, I-1-a-21, I-1-a-22, I-1-a-23, I-1-a-24, I-1-a-25, I-1-a-26,I-1-a-27, I-1-a-28, I-1-a-29, I-1-a-30, I-1-b-2, I-1-b-3, I-1-c-1,I-1-c-2, I-1-c-3, I-2-a-1, I-2-a-2, I-2-a-3, I-2-a-5, I-2-a-6, I-2-a-8,I-2-a-9, I-2-a-10, I-2-a-11, I-2-a-12, I-2-a-7, I-2-a-8, I-2-b-3,I-2-b-9, I-2-b-10, I-2-b-11, I-2-b-12, I-2-b-13, I-2-b-14, I-2-b-15,I-2-b-5, I-2-b-8, I-2-b-16

Example No. 2 Myzus Test MYZUPE Spray Treatment

Solvent: 78.0 parts by weight of acetone  1.5 parts by weight ofdimethylformamide Emulsifier:  0.5 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage (Brassica pekinensis) infested by all stages ofthe green peach aphid (Myzus persicae) are sprayed with an activecompound preparation of the desired concentration.

After the desired period of time, the effect in % is determined. 100%means that all the aphids have been killed; 0% means that none of theaphids have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an effect of ≧80%:

Ex. Nos. I-1-a-1, I-1-a-2, I-1-a-3, I-1-a-5, I-1-a-6, I-1-a-7, I-1-a-8,I-1-a-9, I-1-a-10, I-1-a-11, I-1-a-23, I-1-a-24, I-1-a-25, I-1-a-26,I-1-a-27, I-1-a-28, I-1-a-29, I-1-a-30, I-1-b-2, I-1-b-3, I-1-c-1,I-1-c-2, I-1-c-3, I-2-a-1, I-2-a-2, I-2-a-3, I-2-a-4, I-2-a-5, I-2-a-6,I-2-a-8, I-2-a-9, I-2-a-10, I-2-a-11, I-2-a-12, I-2-b-4, I-2-b-5,I-2-b-8, I-2-b-10, I-2-b-11, I-2-b-12, I-2-b-14, I-2-b-15, I-2-b-16

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an effect of ≧80%:

Ex. Nos. I-1-b-1, I-2-b-6, I-1-a-17

Example No. 3 Tetranychus Test OP-Resistant (TETRUR Spray Treatment)

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of bean leaves (Phaseolus vulgaris) which are infested by allstages of the greenhouse red spidermite (Tetranychus urticae) aresprayed with an active compound preparation of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 g/ha, an effect of ≧80%:see table

Ex. Nos. I-1-a-1, I-1-a-2, I-1-a-3, I-1-a-4, I-1-a-5, I-1-a-6, I-1-a-7,I-1-a-8, I-1-a-9, I-1-a-11, I-1-a-12, I-1-a-16, I-1-a-20, I-1-a-22,I-1-a-23, I-1-a-24, I-1-a-25, I-1-a-29, I-1-a-30, I-1-b-2, I-1-b-3,I-1-c-1, I-1-c-2, I-1-c-3, I-2-a-6, I-2-a-7, I-2-a-8, I-2-a-9, I-2-a-10,I-2-a-11, I-2-a-12, I-2-b-3, I-2-b-4, I-2-b-7, I-2-b-8, I-2-b-10,I-2-b-11, I-2-b-13, I-2-b-14, I-2-b-15

Example No. 4 Spodoptera frugiperda Test SPODFR Spray Treatment

Solvent: 78.0 parts by weight of acetone 1.5 parts by weight ofdimethylformamide Emulsifier: 0.5 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of corn leaves (Zea mays) are sprayed with an active compoundpreparation of the desired concentration and, after drying, populatedwith caterpillars of the armyworm (Spodoptera frugiperda).

After the desired period of time, the effect in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 500 g/ha, an effect of ≧80%:

Ex. Nos. I-1-a-3, I-1-a-6, I-1-a-9, I-1-a-11, I-1-a-19, I-1-a-25,I-1-a-27, I-1-a-29, I-1-b-1, I-1-b-2, I-2-a-3, I-2-a-6, I-2-a-10,I-2-b-10, I-2-b-11, I-2-b-12

Example No. 5 Boophilus microplus Test BOOPMI Injection

Solvent: dimethyl sulfoxide

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water to the desired concentration.

The solution of active compound is injected into the abdomen (Boophilusmicroplus), and the animals are transferred into dishes and kept in aclimatised room. The activity is assessed by oviposition of fertileeggs.

After the desired period of time, the effect in % is determined. 100%means that none of the ticks have laid any fertile eggs.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 μg/animal, an effect of≧80%:

Ex. Nos. I-1-a-1, I-1-a-2, I-1-a-3, I-1-a-5, I-1-a-8, I-1-a-9, I-1-b-1,I-1-b-2, I-1-c-1, I-1-c-2

Example No. 6 Lucilia Cuprina Test LUCICU

Solvent: dimethyl sulfoxide

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water to the desired concentration.

Vessels containing horse meat treated with the active compoundpreparation of the desired concentration are populated with Luciliacuprina larvae.

After the desired period of time, the kill in % is determined. 100%means that all of the larvae have been killed; 0% means that none of thelarvae have been killed.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 100 ppm, an effect of ≧80%:

Ex. Nos. I-1-a-1, I-1-a-3, I-1-a-5, I-1-a-6, I-1-a-8, I-1-a-9, I-1-b-1,I-1-b-2, I-1-c-1, I-1-c-2

Example No. 7 Meloidogyne Test MELGIN Spray Treatment

Solvent: 80 parts by weight of acetone

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water to the desired concentration.

Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

After the desired period of time, the nematicidal action is determinedin % by the gall formation. 100% means that no galls have been found; 0%means that the number of galls on the treated plants corresponds to thatof the untreated control.

In this test, for example, the following compounds of the PreparationExamples show, at an application rate of 20 ppm, an effect of ≧80%:

Ex. Nos. I-1-a-3, I-1-a-7

Example No. 8 Enhancement of Activity by Ammonium/Phosphonium SaltsMyzus persicae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. For application with ammonium or phosphonium salts, theseare added to the spray liquor in a concentration of 1000 ppm.

Bell pepper plants (Capsicum annuum) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying to runoffpoint with the active compound preparation of the desired concentration.After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

TABLE Active Kill rate/% compound after 6 days Active compound ppm +AS(1000 ppm) I-1-a-5 4 5 99

Example No. 9 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium orphosphonium salts, these are added to the spray liquor in aconcentration of 1000 ppm.

Cotton plants (Gossypium hirsutum) which are heavily infested by thecotton aphid (Aphis gossypii) are treated by spraying to runoff pointwith the active compound preparation of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all the aphids have been killed; 0% means that none of theaphids have been killed.

TABLE Active Kill rate/% compound after 6 days Active compound ppm +AS(1000 ppm) I-1-a-1 4 25 95

Example No. 10 Enhancement of Activity by Ammonium/Phosphonium Salts inCombination with Penetrants Myzus persicae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration. For application with ammonium or phosphonium salts andpenetrants (rapeseed oil methyl ester 500 EW) these are added to thespray liquor in each case in a concentration of 1000 ppm.

Bell pepper plants (Capsicum annuum) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by spraying to runoffpoint with the active compound preparation of the desired concentration.After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

TABLE Kill rate/% after 6 days +RME + Active Concentration/ +AS +RME AS(1000 compound ppm (1000 ppm) (1000 ppm) ppm each) I-1-a-1 4 95 90 99100 I-1-a-1 0.8 0 0 0 95

Example No. 11 Aphis gossypii Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 part byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration. For application with ammonium orphosphonium salts and penetrants (rapeseed oil methyl esters 500 EW)these are added to the spray liquor in each case in a concentration of1000 ppm.

Cotton plants (Gossypium hirsutum) which are heavily infested by thecotton aphid (Aphis gossypii) are treated by spraying to runoff pointwith the active compound preparation of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all the aphids have been killed; 0% means that none of theaphids have been killed.

TABLE Kill rate/% after 6 days +RME + Active Concentration/ +AS +RME AS(1000 compound ppm (1000 ppm) (1000 ppm) ppm each) I-1-a-3 20 25 5 10 90I-1-a-3 4 0 0 5 25

Example No. 12 Heliothis virescens Test Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone Emulsifier: 1 parts by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soybean shoots (Glycine max) of the cultivar Roundup Ready (trade nameof Monsanto Comp. USA) are treated by being dipped into the preparationof active compound of the desired concentration and are populated withthe tobacco bud worm Heliothis virescens while the leaves are stillmoist.

After the desired period of time, the kill of the insects is determined.

Example No. 13 Critical Concentration Test/Soil Insects Treatment ofTransgenic Plants

Test insect: Diabrotica balteata - larvae in soil Solvent: 7 parts byweight of acetone Emulsifier: 1 parts by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of active compound in the preparation is virtuallyirrelevant, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l) matters. The soil is filled into0.25 l pots and these are allowed to stand at 20° C.

Immediately after preparation, 5 pre-germinated corn corms of thecultivar YIELD GUARD (trade mark of Monsanto Comp., LISA) are placedinto each pot. After 2 days, the test insects in question are placedinto the treated soil. After a further 7 days, the efficacy of theactive compound is determined by counting the corn plants that haveemerged (1 plant=20% efficacy).

Example No. 14 1. Herbicidal Pre-Emergence Action

-   -   Seeds of monocotyledonous and dicotyledonous weed and crop        plants are placed in sandy loam in wood fiber pots and covered        with soil. The test compounds, formulated in the form of        wettable powders (WP) are then, as an aqueous suspension with a        water application rate of 600 l/ha (converted), with 0.2% of        wetting agent added, applied at various dosages to the surface        of the covering soil.

After the treatment, the pots are placed in a greenhouse and kept undergood growth conditions for the test plants. The visual assessment of theemergence damage to the test plants is carried out after a trial periodof 3 weeks by comparison with untreated controls (herbicidal activity inpercent: 100% activity=the plants have died, 0% activity=like controlplants).

In addition to the compounds mentioned above, the following compoundsshow a pre-emergence action of ≧80% against Lolium multiflorum andSetaria viridis at 320 g/ha of a.i.: I-1-a-1, I-1-a-2, I-1-a-4, I-1-a-5,I-1-a-7, I-1-a-8, I-1-a-9, I-1-a-12, I-1-a-13, I-1-a-14, I-1-b-1,I-1-b-3, I-1-c-1, I-1-c-2, I-1-c-3.

2. Herbicidal Post-Emergence Action

-   -   Seeds of monocotyledonous and dicotyledonous weed and crop        plants are placed in sandy loam in wood fiber pots, covered with        soil and cultivated in a greenhouse under good growth        conditions. 2 to 3 weeks after sowing, the test plants are        treated at the one-leaf stage. The test compounds, formulated as        wettable powders (WP) are then, with a water application rate of        600 l/ha (converted), with 0.2% of wetting agent added, sprayed        at various dosages onto the green parts of the plants. After the        test plants have been kept in the greenhouse under optimum        growth conditions for about 3 weeks, the activity of the        preparations is rated visually in comparison to untreated        controls (herbicidal activity in percent: 100% activity=the        plants have died, 0% activity=like control plants).    -   In addition to the compounds mentioned above, the following        compounds show a post-emergence action of ≧80% against        Echinocloa crus-galli, Lolium multiflorum and Setaria viridis at        80 g/ha: I-1-a-2, I-1-a-4, I-1-a-5, I-1-a-7, I-1-a-9, I-1-a-12,        I-1-a-13, I-1-a-14, I-1-b-3.

Use of Safeners:

-   -   If it is additionally to be tested as to whether safeners can        improve the plant compatibility of test substances in the case        of crop plants, the following options are used for applying the        safeners:        -   seeds of the crop plants are, before sowing, dressed with            the safener substance (the amount of safener stated in            percent, based on the weight of the seed)        -   before application of the test substances, the crop plants            are sprayed with the safener at a certain application rate            per hectare (usually 1 day before the application of the            test substances)        -   the safener is applied together with the test substance as a            tank mix (the amount of safener stated in g/ha or as a            ratio, based on the herbicide).

TABLE Application 10 days after 28 days after application rateapplication Summer Summer wheat observed g a.i./ha wheat observed (%)(%) Ex. 100 60 40 (I-1-a-7) 50 60 30 25 50 20 12.5 40 10 Ex. (I-1- 100 +50  40 20 a-7) + 50 + 50 40 20 mefenpyr 25 + 50 30 10 12.5 + 50   25 0

-   -   Application of the safener 1 day prior to the herbicide

1. A compound of the formula (I)

in which W represents hydrogen, alkyl, alkenyl, alkynyl, optionallysubstituted cycloalkyl, halogen, alkoxy, alkenyloxy, haloalkyl,haloalkoxy or cyano, X represents halogen, alkyl, alkenyl, alkynyl,optionally substituted cycloalkyl, alkoxy, alkenyloxy, alkylthio,alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy,nitro or cyano, Y and Z independently of one another represent hydrogen,alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl, alkoxy,halogen, haloalkyl, haloalkoxy, cyano, nitro or in each case optionallysubstituted aryl or hetaryl, A represents haloalkoxy orhalocycloalkylalkoxy, D represents NH or oxygen, Q¹, Q³ independently ofone another represent hydrogen, alkyl, haloalkyl or alkoxy, m representsthe number 0 or 1, G represents hydrogen (a) or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulfur, M represents oxygen or sulfur, R¹ represents in eachcase optionally halogen- or cyano-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or represents in eachcase optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl orheterocyclyl or represents in each case optionally substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents ineach case optionally halogen- or cyano-substituted alkyl, alkenyl,alkoxyalkyl or polyalkoxyalkyl or represents in each case optionallysubstituted cycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵ independently ofone another represent in each case optionally halogen-substituted alkyl,alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio orcycloalkylthio or represent in each case optionally substituted phenyl,benzyl, phenoxy or phenylthio, R⁶ and R⁷ independently of one anotherrepresent hydrogen, in each case optionally halogen- orcyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, ineach case optionally substituted phenyl or benzyl, or together with theN atom to which they are attached form an optionally substituted cyclewhich optionally contains oxygen or sulfur.
 2. The compound of theformula (I) as claimed in claim 1 in which W represents hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, represents C₃-C₆-cycloalkylwhich is optionally mono- or disubstituted by C₁-C₂-alkyl, alkoxy,fluorine, chlorine, trifluoromethyl or C₃-C₆-cycloalkyl, representshalogen, C₁-C₆-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano, Xrepresents halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,represents C₃-C₆-cycloalkyl which is optionally mono- or disubstitutedby C₁-C₂-alkyl, C₁-C₂-alkoxy, fluorine, chlorine, trifluoromethyl orC₃-C₆-cycloalkyl, represents C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkoxy, C₃-C₆-haloalkenyloxy, nitro orcyano, Y and Z independently of one another represent hydrogen, halogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, represent C₃-C₆-cycloalkylwhich is optionally mono- or disubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy,fluorine, chlorine, trifluoromethyl or C₃-C₆-cycloalkyl, representC₁-C₆-alkoxy, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, cyano, C₂-C₆-alkenyl,C₂-C₆-alkynyl or one of the (het)aryl radicals

where in the case of (het)aryl only one of the radicals Y or Z mayrepresent (het)aryl, V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, nitro, cyano, or represents phenyl,phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio, each of which isoptionally monosubstituted or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, haloalkyl, C₁-C₄-haloalkoxy, nitro or cyano, V² and V³independently of one another represent hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy, A representsC₁-C₄-alkoxy which is mono- to heptasubstituted by fluorine, chlorine,bromine and/or iodine or represents C₃-C₆-cycloalkyl-C₁-C₂-alkoxy whichis mono- to pentasubstituted by fluorine, chlorine and/or bromine andwhich may optionally be substituted by C₁-C₂-alkyl, C₁-C₂-haloalkyl orC₁-C₂-alkoxy, D represents NH (1) or oxygen (2), Q¹ and Q² independentlyof one another represent hydrogen, C₁-C₆-alkyl, C₁-C₂-haloalkyl orC₁-C₄-alkoxy, m represents the number 0 or 1, G represents hydrogen (a)or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulfur and M represents oxygen or sulfur, R¹ represents ineach case optionally halogen- or cyano-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one or twonot directly adjacent methylene groups are replaced by oxygen and/orsulfur, represents phenyl which is optionally substituted by halogen,cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl, representsphenyl-C₁-C₆-alkyl which is optionally substituted by halogen, nitro,cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy,represents optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl having one or two heteroatoms from the groupconsisting of oxygen, sulfur and nitrogen, representsphenoxy-C₁-C₆-alkyl which is optionally substituted by halogen orC₁-C₆-alkyl, represents optionally halogen-, amino- orC₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl havingone or two heteroatoms from the group consisting of oxygen, sulfur andnitrogen, R² represents in each case optionally halogen- orcyano-substituted C₁-C₂₀ alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkylor poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, or represents C₃-C₈-cycloalkyl whichis optionally substituted by halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy, orrepresents phenyl or benzyl, each of which is optionally substituted byhalogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl orC₁-C₆-halogenalkoxy, R³ represents optionally halogen-substitutedC₁-C₈-alkyl or in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-haloalkyl-, C₁-C₄-haloalkoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of oneanother represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di(C₁-C₈-alkyl)amino,C₁-C₈-alkylthio or C₃-C₈-alkenylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-haloalkoxy-,C₁-C₄-alkylthio-, C₁-C₄-haloalkylthio-, C₁-C₄-alkyl- orC₁-C₄-haloalkyl-substituted phenyl, phenoxy or phenylthio, R⁶ and R⁷independently of one another represent hydrogen, represent in each caseoptionally halogen- or cyano-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl,C₁-C₈-alkoxy, C₃-C₈-alkenyl or C₁-C₈-alkoxy-C₂-C₈-alkyl, represent ineach case optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-haloalkyl- orC₁-C₈-alkoxy-substituted phenyl or benzyl or together represent anoptionally C₁-C₆-alkyl-substituted C₃-C₆-alkylene radical in whichoptionally one methylene group is replaced by oxygen or sulfur.
 3. Thecompound of the formula (I) as claimed in claim 1 in which W representshydrogen, chlorine, bromine, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄alkynyl,represents C₃-C₆-cycloalkyl which is optionally monosubstituted bymethyl, ethyl, methoxy, fluorine, chlorine, trifluoromethyl orcyclopropyl, represents C₁-C₄-alkoxy, C₁-C₂-haloalkyl orC₁-C₂-haloalkoxy, X represents chlorine, bromine, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄alkynyl, represents C₃-C₆-cycloalkyl which isoptionally monosubstituted by methyl, ethyl, methoxy, fluorine,chlorine, trifluoromethyl or cyclopropyl, represents C₁-C₄-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy or cyano, Y and Z independently of oneanother represent hydrogen, fluorine, chlorine, bromine, C₁-C₄ alkylC₂-C₄-alkenyl, C₂-C₄-alkynyl, represent C₃-C₆-cycloalkyl which isoptionally monosubstituted by methyl, ethyl, methoxy, fluorine,chlorine, trifluoromethyl or cyclopropyl, represents C₁-C₆-alkoxy,C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano, C₂-C₄-alkenyl, C₂-C₄-alkynylor one of the (het)aryl radicals,

where in the case of (het)aryl only one of the radicals Y or Z mayrepresent (het)aryl, V¹ represents hydrogen, fluorine, chlorine,bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy,nitro, cyano or represents phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy, nitro or cyano, V² and V³independently of one another represent hydrogen, fluorine, chlorine,bromine, C₁-C₄ alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkyl or C₁-C₂-haloalkoxy,A represents C₁-C₄-alkoxy which is mono- to pentasubstituted byfluorine, chlorine and/or bromine or representsC₃-C₆-cycloalkyl-C₁-C₂-alkoxy which is mono- to trisubstituted byfluorine and/or chlorine, D represents NH (1) or oxygen (2), Q¹ and Q²independently of one another represent hydrogen, methyl, ethyl,trifluoromethyl, methoxy or ethoxy, m represents the number 0 or 1, Grepresents hydrogen (a) or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulfur and M represents oxygen or sulfur, R¹ representsC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆ alkoxy C₁-C₄ alkyl,C₁-C₆-alkylthio-C₁-C₄-alkyl or poly-C₁-C₆-alkoxy-C₁-C₄-alkyl, each ofwhich is optionally mono- to trisubstituted by fluorine or chlorine, orrepresents C₃-C₇-cycloalkyl which is optionally mono- or disubstitutedby fluorine, chlorine, C₁-C₅-alkyl or C₁-C₅-alkoxy and in whichoptionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulfur, represents phenyl which is optionallymono- to trisubstituted by fluorine, chlorine, bromine, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy,C₁-C₄-alkylthio or C₁-C₄-alkylsulfonyl, represents phenyl-C₁-C₄-alkylwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₃-haloalkyl or C₁-C₃-haloalkoxy,represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine or C₁-C₄-alkyl, represents phenoxy-C₁-C₅-alkyl whichis optionally mono- or disubstituted by fluorine, chlorine, bromine orC₁-C₄-alkyl or represents pyridyloxy-C₁-C₅-alkyl,pyrimidyloxy-C₁-C₅-alkyl or thiazolyloxy-C₁-C₅-alkyl, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine, aminoor C₁-C₄-alkyl, R² particularly preferably represents C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₂-C₆-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, represents C₃-C₇-cycloalkylwhich is optionally mono- or disubstituted by fluorine, chlorine,C₁-C₄-alkyl or C₁-C₄-alkoxy or represents phenyl or benzyl, each ofwhich is optionally mono- to trisubstituted by fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl orC₁-C₃-haloalkoxy, R³ represents C₁-C₆-alkyl which is optionally mono- totrisubstituted by fluorine or chlorine or represents phenyl or benzyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy,C₁-C₂-haloalkyl, cyano or nitro, R⁴ and R⁵ independently of one anotherrepresent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio, each ofwhich is optionally mono- to trisubstituted by fluorine or chlorine, orrepresent phenyl, phenoxy or phenylthio, each of which is optionallymono- or disubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio,C₁-C₃-alkyl or C₁-C₃-haloalkyl, R⁶ and R⁷ independently of one anotherrepresent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine, representphenyl or benzyl, each of which is optionally mono- to trisubstituted byfluorine, chlorine, bromine, C₁-C₅-haloalkyl, C₁-C₅-alkyl orC₁-C₅-alkoxy, or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onemethylene group is replaced by oxygen or sulfur.
 4. The compound of theformula (I) as claimed in claim 1 in which W represents hydrogen,chlorine, bromine, methyl, ethyl, vinyl, ethynyl, propynyl, cyclopropyl,methoxy, ethoxy or trifluoromethyl, X represents chlorine, bromine,methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, propynyl, cyclopropyl,methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy orcyano, Y and Z independently of one another represent hydrogen,fluorine, chlorine, bromine, methyl, ethyl, vinyl, ethynyl, propynyl,cyclopropyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or aphenyl radical,

where in the case of phenyl only one of the radicals Y or Z mayrepresent phenyl, V¹ represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy,n-propoxy, isopropoxy, trifluoromethyl or trifluoromethoxy, V²represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl,isopropyl, methoxy, ethoxy or trifluoromethyl, A represents methoxy,ethoxy, propoxy, butoxy or isobutoxy, each of which is mono- totrisubstituted by fluorine and/or chlorine, or representscyclopropylmethoxy or cyclopropylethoxy, each of which is mono- totrisubstituted by fluorine and/or chlorine, D represents NH (1) oroxygen (2), Q¹ and Q² represent hydrogen, m represents the number 1, Grepresents hydrogen (a) or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulfur and M represents oxygen or sulfur, R¹ representsC₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine, or represents C₃-C₆-cycloalkylwhich is optionally monosubstituted by fluorine, chlorine, methyl, ethylor methoxy, represents phenyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl,isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,represents furanyl, thienyl or pyridyl, each of which is optionallymonosubstituted by chlorine, bromine or methyl, R² representsC₁-C₁₀-alkyl, C₂-C₁₀-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine,represents cyclopentyl or cyclohexyl, or represents phenyl or benzyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl ortrifluoromethoxy, R³ represents methyl, ethyl, propyl or isopropyl, eachof which is optionally mono- to trisubstituted by fluorine or chlorine,or represents phenyl which is optionally monosubstituted by fluorine,chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy,ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,R⁴ and R⁵ independently of one another represent C₁-C₄-alkoxy orC₁-C₄-alkylthio or represent phenyl, phenoxy or phenylthio, each ofwhich is optionally monosubstituted by fluorine, chlorine, bromine,nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy, R⁶and R⁷ independently of one another represent hydrogen, C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, represent phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy ortrifluoromethyl, or together represent a C₅-C₆-alkylene radical in whichoptionally one methylene group is replaced by oxygen or sulfur.
 5. Thecompound of the formula (I) as claimed in claim 1 in which W representshydrogen, chlorine, bromine, methyl, ethyl or methoxy, X representschlorine, bromine, methyl, ethyl, methoxy or ethoxy, Y and Zindependently of one another represent hydrogen, chlorine, bromine,methyl, methoxy, cyclopropyl or represent the radicals

where in this case only one of the radicals Y or Z may represent asubstituted phenyl radical, A represents methoxy, ethoxy or propoxy,each of which is mono- to trisubstituted by fluorine and/or chlorine, Drepresents NH (1) or oxygen (2), Q¹ and Q² represent hydrogen, mrepresents the number 1, G represents hydrogen (a) or one of the groups

R¹ represents C₁-C₁₀-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₃-C₆-cycloalkyl,represents phenyl which is optionally monosubstituted by chlorine, orrepresents thienyl, R² represents C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, orrepresents benzyl, R³ represents methyl, R⁶ and R⁷ together represent aC₅-C₆-alkylene radical in which optionally one methylene group isreplaced by oxygen or sulfur.
 6. A process for the preparation of acompound of the formula (I) as claimed in claim 1, characterized inthat, to obtain (A) compounds of the formula (I-1-a)

in which A, Q¹, Q², m, W, X, Y and Z have the meanings given above,compounds of the formula (II)

in which A, Q¹, Q², m, W, X, Y and Z have the meanings given above, andR⁸ represents alkyl, are subjected to an intramolecular condensationreaction in the presence of a diluent and in the presence of a base, (B)compounds of the formula (I-2-a)

in which A, Q¹, Q², m, W, X, Y and Z have the meanings given above,compounds of the formula (III)

in which A, Q¹, Q², m, W, X, Y, Z and R⁸ have the meanings given above,are subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base, (C) compounds of theformulae (I-1-b) to (I-2-b) shown above in which R¹, A, Q¹, Q², m, W, X,Y and Z have the meanings given above, compounds of the formulae (I-1-a)to (I-2-a) in which A, Q¹, Q², m, W, X, Y and Z have the meanings givenabove are in each case α) reacted with compounds of the formula (IV)

in which R¹ has the meaning given above and Hal represents halogen or β)with carboxylic anhydrides of the formula (V)R¹—CO—O—CO—R¹  (V) in which R¹ has the meaning given above, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder; (D) compounds of the formulae (I-1-c) to(I-2-c) shown above in which R², A, Q¹, Q², m, W, M, X, Y and Z have themeanings given above, and L represents oxygen, compounds of the formulae(I-1-a) to (I-2-a) shown above in which A, Q¹, Q², m, W, X, Y and Z havethe meanings given above are in each case reacted with chloroformicesters or chloroformic thioesters of the formula (VI)R²—M—CO—Cl  (VI) in which R² and M have the meanings given above, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder; (E) compounds of the formulae (I-1-c) to(I-2-c) shown above in which R², A, Q¹, Q², m, W, M, X, Y and Z have themeanings given above, and L represents sulfur, compounds of the formulae(I-1-a) to (I-2-a) shown above in which A, Q¹, Q², m, W, X, Y and Z havethe meanings given above are in each case reacted withchloromonothioformic esters or chlorodithioformic esters of the formula(VII)

in which M and R² have the meanings given above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder, (F) compounds of the formulae (I-1-d) to (I-2-d) shown above inwhich R³, A, W, Q¹, Q², m, X, Y and Z have the meanings given above,compounds of the formulae (I-1-a) to (I-2-a) shown above in which A, B,Q¹, Q², m, W, X, Y and Z have the meanings given above are in each casereacted with sulfonyl chlorides of the formula (VIII)R³—SO₂—Cl  (VIII) in which R³ has the meaning given above, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder, (G) compounds of the formulae (I-1-e) to(I-2-e) shown above in which L, R⁴, R⁵, A, Q¹, Q², m, W, X, Y and Z havethe meanings given above, compounds of the formulae (I-1-a) to (I-2-a)shown above in which A, Q¹, Q², m, W, X, Y and Z have the meanings givenabove are in each case reacted with phosphorus compounds of the formula(IX)

in which L, R⁴ and R⁵ have the meanings given above and Hal representshalogen if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, (H) compounds of the formulae (I-1-f)to (I-2-f) shown above in which E, A, Q¹, Q², m, W, X, Y and Z have themeanings given above, compounds of the formulae (I-1-a) to (I-2-a) inwhich A, Q¹, Q², y m, W, X, Y and Z have the meanings given above are ineach case reacted with metal compounds or amines of the formulae (X) or(XI)

in which Me represents a monovalent or divalent metal, t represents thenumber 1 or 2 and R¹⁰, R¹¹, R¹² independently of one another representhydrogen or alkyl, if appropriate in the presence of a diluent, (I)compounds of the formulae (I-1-g) to (I-2-g) shown above in which L, R⁶,R⁷, A, Q¹, Q², M, W, X, Y and Z have the meanings given above, compoundsof the formulae (I-1-a) to (I-2-a) shown above in which A, Q¹, Q², m, W,X, Y and Z have the meanings given above are in each case α) reactedwith isocyanates or isothiocyanates of the formula (XII)R⁶—N═C=L  (XII) in which R⁶ and L have the meanings given above, ifappropriate in the presence of a diluent and if appropriate in thepresence of a catalyst, or β) reacted with carbamoyl chlorides orthiocarbamoyl chlorides of the formula (XIII)

in which L, R⁶ and R⁷ have the meanings given above, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder, (Jα) compounds of the formulae (I-1-a) to (I-1-g) shown above inwhich A, D, G, Q¹, Q², m, W, X, Y and Z have the meaning given above,compounds of the formulae (I-1-a′) to (I-2-g′) in which A, D, G, Q¹, Q²,m, W, X and Y have the meaning given above and Z′ represents bromine oriodine

and (Jβ) compounds of the formulae (I-1-a) to (I-2-g) shown above inwhich A, D, G, Q¹, Q², m, W, X, Y and Z have the meaning given above,compounds of the formulae (I-1-a″) to (I-2-g″) in which A, D, G, Q¹, Q²,m, W, X and Z have the meaning given above and Y′ represents bromine oriodine

are coupled with (het)aryl derivatives of the formulae (XVα) and (XVβ)

or esters thereof, in the presence of a solvent, in the presence of acatalyst and in presence of a base.
 7. A composition for controllingpests and/or unwanted vegetation, characterized in that it comprises atleast one compound of the formula (I) as claimed in claim
 1. 8. A methodof controlling animal pests and/or unwanted vegetation, characterized inthat a compound of the formula (I) as claimed in claim 1 is allowed toact on pests, unwanted vegetation and/or their habitat.
 9. The use of acompound of the formula (I) as claimed in claim 1 for controlling animalpests and/or unwanted vegetation.
 10. A process for preparingcompositions for controlling pests and/or unwanted vegetation,characterized in that a compound of the formula (I) as claimed in claim1 is mixed with extenders and/or surfactants.
 11. The use of a compoundof the formula (I) as claimed in claim 1 for preparing compositions forcontrolling pests and/or unwanted vegetation.
 12. A compositioncomprising an effective amount of an active compound combinationcomprising, as components, (a′) at least one compound of the formula (I)in which A, D, G, Q¹, Q², m, W, X, Y and Z have the meaning given aboveand (b′) at least one crop plant compatibility-improving compound fromthe following group of compounds:4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67, MON-4660),1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one(dicyclonon, BAS-145138),4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),1-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl—cf.also related compounds in EP-A-86750, EP-A-94349, EP-A-191736,EP-A-492366), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea(cumyluron), α-(cyanomethox-imino)phenylacetonitrile (cyometrinil),2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyricacid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea(daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba),S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate (dimepiperate),2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide(DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid),4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate(fenchlorazole-ethyl—cf. also related compounds in EP-A-174562 andEP-A-346620), phenylmethyl2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole),4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime(fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine(furilazole, MON-13900), ethyl4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl—cf.also related compounds in WO-A-95/07897), 1-(ethoxycarbonyl)ethyl3,6-dichloro-2-methoxybenzoate (lactidichlor),(4-chloro-o-tolyloxy)acetic acid (MCPA),2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), diethyl1-(2,4-dichlorophenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate(mefenpyr-diethyl—cf. also related compounds in WO-A-91/07874),2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),2-propenyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838),1,8-naphthalic anhydride,α-(1,3-dioxolan-2-ylmethoximino)phenylacetonitrile (oxabetrinil),2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide(PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725),3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148),4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid,diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyldiphenylmethoxyacetate, methyl1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate,ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate (cf.also related compounds in EP-A-269806 and EP-A-333131), ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl5-phenyl-2-isoxazoline-3-carboxylate, ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (cf. alsorelated compounds in WO-A-91/08202), 1,3-dimethylbut-1-yl5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate,ethyl 5-chloroquinoline-8-oxyacetate, allyl5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate,diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl5-chloroquinoline-8-oxymalonate (cf. also related compounds inEP-A-582198), 4-carboxychroman-4-ylacetic acid (AC-304415, cf.EP-A-613618), 4-chlorophenoxyacetic acid,3,3′-dimethyl-4-methoxybenzophenone,1-bromo-4-chloromethylsulfonylbenzene,1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known asN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide),1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,1-[4-(N-naphthylsulfamoyl)phenyl]-3,3-dimethylurea,N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylamino-carbonyl)benzenesulfonamide,and/or one of the following compounds, defined by general formulae, ofthe general formula (IIa)

or of the general formula (IIb)

or of the formula (IIc)

when m represents a number 0, 1, 2, 3, 4 or 5, A¹ represents one of thedivalent heterocyclic groupings shown below,

n represents a number 0, 1, 2, 3, 4 or 5, A² represents optionallyC₁-C₄-alkyl- and/or C₁-C₄-alkoxycarbonyl- and/orC₁-C₄-alkenyloxycarbonyl-substituted alkanediyl having 1 or 2 carbonatoms, R¹⁴ represents hydroxyl, mercapto, amino, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino, R¹⁵represents hydroxyl, mercapto, amino, C₁-C₇-alkoxy, C₁-C₆-alkylthio,C₁-C₆-alkenyloxy, C₁-C₆-alkenyloxy-C₁-C₆-alkoxy, C₁-C₆-alkylamino ordi(C₁-C₄-alkyl)amino, R¹⁶ represents optionally fluorine-, chlorine-and/or bromine-substituted C₁-C₄-alkyl, R¹⁷ represents hydrogen, in eachcase optionally fluorine-, chlorine- and/or bromine-substitutedC₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, R¹⁸ represents hydrogen, in each caseoptionally fluorine-, chlorine- and/or bromine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl or C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄alkyl,dioxolanyl-C₁-C₄-alkyl, furyl, furyl-C₁-C₄-alkyl, thienyl, thiazolyl,piperidinyl, or optionally fluorine-, chlorine- and/or bromine- orC₁-C₄-alkyl-substituted phenyl, R¹⁷ and R¹⁸ also together representC₃-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, each of which is optionallysubstituted by C₁-C₄-alkyl, phenyl, furyl, a fused benzene ring or bytwo substituents which, together with the C atom to which they areattached, form a 5- or 6-membered carbocycle, R¹⁹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, R²⁰ represents hydrogen, in each case optionally hydroxyl-,cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₃-C₆-cycloalkyl or tri-(C₁-C₄-alkyl)silyl, R²¹ represents hydrogen,cyano, halogen, or represents in each case optionally fluorine-,chlorine- and/or bromine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl orphenyl, X¹ represents nitro, cyano, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄haloalkoxy, X² representshydrogen, cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy or C₁-C₄-haloalkoxy, X³ represents hydrogen, cyano, nitro,halogen, C₁-C₄-alkyl, C₁-C₄ haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy,and/or the following compounds, defined by general formulae, of thegeneral formula (IId)

or of the general formula (IIe)

where t represents a number 0, 1, 2, 3, 4 or 5, v represents a number 0,1, 2, 3, 4 or 5, R²² represents hydrogen or C₁-C₄-alkyl, R²³ representshydrogen or C₁-C₄-alkyl, R²⁴ represents hydrogen, in each caseoptionally cyano-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino or di(C₁-C₄-alkyl)amino,or in each case optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, C₃-C₆-cycloalkyloxy, C₃-C₆-cycloalkylthio orC₃-C₆-cycloalkylamino, R²⁵ represents hydrogen, optionally cyano-,hydroxyl-, halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in eachcase optionally cyano- or halogen-substituted C₃-C₆-alkenyl orC₃-C₆-alkynyl, or optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedC₃-C₆-cycloalkyl, R²⁶ represents hydrogen, optionally cyano-, hydroxyl-,halogen- or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl, in each caseoptionally cyano- or halogen-substituted C₃-C₆-alkenyl or C₃-C₆-alkynyl,optionally cyano-, halogen- or C₁-C₄-alkyl-substituted C₃-C₆-cycloalkyl,or optionally nitro-, cyano-, halogen-, C₁-C₄-alkyl-,C₁-C₄-halo-C₁-C₄-alkoxy- or C₁-C₄-haloalkoxy-substituted phenyl, ortogether with R²⁵ represents in each case optionallyC₁-C₄-alkyl-substituted C₂-C₆-alkanediyl or C₂-C₅-oxaalkanediyl, X⁴represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl,hydroxyl, amino, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy, and X⁵ represents nitro, cyano, carboxyl, carbamoyl,formyl, sulfamoyl, hydroxyl, amino, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy.
 13. The compositionas claimed in claim 12 where the crop plant compatibility-improvingcompound is selected from the following group of compounds:cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron or thecompounds


14. The composition as claimed in claim 12 or 13 where the crop plantcompatibility-improving compound is cloquintocet-mexyl.
 15. Thecomposition as claimed in claim 12 or 13 where the crop plantcompatibility-improving compound is mefenpyr-diethyl.
 16. A method forcontrolling unwanted vegetation, characterized in that a composition asclaimed in claim 12 is allowed to act on the plants or theirsurroundings.
 17. The use of a composition as claimed in claim 12 forcontrolling unwanted vegetation.
 18. A method for controlling unwantedvegetation, characterized in that a compound of the formula (I) asclaimed in claim 1 and the crop plant compatibility-improving compoundas set forth in claim 12 are allowed to act separately, in closetemporal succession on the plants or their surroundings.
 19. Acomposition, comprising at least one compound of the formula (I) asclaimed in claim 1 or a composition as claimed in claim 12 and at leastone salt of the formula (III′)

in which D represents nitrogen or phosphorus, R²⁶, R²⁷, R²⁸ and R²⁹independently of one another represent hydrogen or in each caseoptionally substituted C₁-C₈-alkyl or mono- or polyunsaturated,optionally substituted C₁-C₈-alkylene, the substituents being selectablefrom halogen, nitro and cyano, n represents 1, 2, 3 or 4, R³⁰ representsan inorganic or organic anion.
 20. A composition as claimed in claim 19,characterized in that it comprises at least one penetrant.
 21. A methodof increasing the activity of pesticides and/or herbicides comprising anactive compound of the formula (I) as claimed in claim 1 or acomposition as claimed in claim 12, characterized in that theready-to-use material (spray liquor) is prepared using a salt of theformula (III′) as claimed in claim
 19. 22. The method as claimed inclaim 21, characterized in that the spray liquor is prepared using apenetrant.
 23. A compound of the formula (II)

in which A, m, Q¹, Q², W, X, Y and Z have the meaning given above.
 24. Acompound of the formula (III)

in which A, m, Q¹, Q², W, X, Y, Z and R⁸ have the meaning given above.25. A compound of the formula (XVI)

in which A, m, Q¹, Q² and R⁸ have the meaning given above.
 26. Acompound of the formula (XVIII)

in which A, Q¹, Q², m, W, X, Y and Z have the meaning given above.
 27. Acompound of the formula (XIX)

in which A, m, Q¹ and Q² have the meaning given above.
 28. A compound ofthe formula (XXI)

in which A, m, Q¹, Q², W, X, Y and Z have the meaning given above.
 29. Acompound of the formula (XXII)

in which A, m, Q¹, Q² and R⁸ have the meaning given above.
 30. Acompound of the formula (XXIII-1)